Sodium borohydride → HCID 90014140, compound

HRID 1486839Notes

Reaction equation

HRID 1486839 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[C:21]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([C:22]5[CH:27]=[CH:26][C:25]([N:28]6[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]6)=[CH:24][CH:23]=5)[CH:19]=4)[NH:14][C:13]=3[N:12]=[CH:11][CH:10]=2)[C:6]([O:35][CH3:36])=[CH:5][C:4]=1[C:37]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:38].[BH4-].[Na+]>C(Cl)Cl.CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[C:21]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([C:22]5[CH:23]=[CH:24][C:25]([N:28]6[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]6)=[CH:26][CH:27]=5)[CH:19]=4)[NH:14][C:13]=3[N:12]=[CH:11][CH:10]=2)[C:6]([O:35][CH3:36])=[CH:5][C:4]=1[CH:37]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[OH:38]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 90013527HCID 90013527, compound

Product 1

HCID 90014140HCID 90014140, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of (2,5-dimethoxy-4-(6-(4-(4-methylpiperazin-1-yl)phenyl)-9H-pyrido[2,3-b]indol-4-yl)phenyl)(phenyl)methanone (example 50, 39.8 mg, 0.0683 mmol) in CH2Cl2/MeOH 5:2 (2 mL), NaBH4 (6 mg, 2.3 eq) was added. After stirring for 1 h20 at r.t., the reaction mixture was quenched with sat. aq. NH4Cl (5 mL), diluted with CH2Cl2 (25 mL) and washed with water (30 mL) The organic layer was collected and the aqueous layer washed four times with CH2Cl2 (20 mL) The combined organic layers were washed with brine and dried over MgSO4, filtered and evaporated to dryness. A white solid was obtained in 66% yield (26.3 mg) after trituration of the crude product in DCM and filtration. 1H NMR (300 MHz, DMSO, 80° C.) δ 11.61 (s, 1H), 8.41 (d, J=5.0 Hz, 1H), 7.63 (dd, J=8.4, 1.9 Hz, 1H), 7.51 (d, J=8.4 Hz, 1H), 7.49-7.41 (m, 4H), 7.35-7.15 (m, 5H), 7.08 (d, J=5.0 Hz, 1H), 7.02 (s, 1H), 6.98-6.79 (m, 2H), 6.11 (d, J=4.9 Hz, 1H), 5.67 (d, J=5.4 Hz, 1H), 3.69 (s, 3H), 3.62 (s, 3H), 3.24-3.14 (m, 4H), 2.54-2.47 (m, 4H), 2.27 (s, 3H); 13C NMR (75 MHz, DMSO, 80° C.) δ 152.2 (C), 150.2 (C), 149.6 (C), 149.2 (C), 145.2 (CH), 144.8 (C), 140.6 (C), 137.6 (C), 135.1 (C), 131.0 (C), 131.0 (C), 127.5 (CH), 126.3 (CH), 126.2 (CH), 126.1 (CH), 125.9 (C), 124.3 (CH), 121.8 (C), 120.7 (C), 118.6 (CH), 116.1 (CH), 115.3 (CH), 113.4 (CH), 111.0 (CH), 110.6 (CH), 68.1 (CH), 55.9 (OCH3), 55.8 (OCH3), 54.3 (2CH2), 47.8 (2CH2), 45.3 (NCH3); MS (ESI) m/z: 585.5 [M+H]+; 1170.1 [2M+H]+; 567.3 [M-OH]+; HRMS calcd for C37H37N4O3 [M+H]+ 585.2860 found 585.2868.

Workup

  1. customthe reaction mixture was quenched with sat. aq. NH4Cl (5 mL)
  2. additiondiluted with CH2Cl2 (25 mL)
  3. washwashed with water (30 mL) The organic layer
  4. customwas collected
  5. washthe aqueous layer washed four times with CH2Cl2 (20 mL) The combined organic layers
  6. washwere washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customA white solid was obtained in 66% yield (26.3 mg)
  11. filtrationafter trituration of the crude product in DCM and filtration

Sources & evidence

ORD record
ord-4929eeb8c7fc41999cc3804c663962c0
Source dataset
uspto-grants-2016_08
Patent number
US09428500B2

Reaction notes

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