Tetrahydrofuran → HCID 66604015, compound

HRID 2410911Notes

Reaction equation

HRID 2410911 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([C:28]([NH2:30])=[O:29])[C:12]3[NH:13][C:14]4[C:19]([C:20]=3[CH:21]=2)=[CH:18][CH:17]=[C:16]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH:15]=4)=[CH:5][C:4]=1[CH3:31])=O.[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C1COCC1>C(Cl)Cl>[CH3:31][C:4]1[CH:5]=[C:6]([C:9]2[CH:10]=[C:11]([C:28]([NH2:30])=[O:29])[C:12]3[NH:13][C:14]4[C:19]([C:20]=3[CH:21]=2)=[CH:18][CH:17]=[C:16]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[CH:15]=4)[CH:7]=[CH:8][C:3]=1[CH2:1][N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 86663074HCID 86663074, compound

Product 1

HCID 66604015HCID 66604015, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-formyl-3-methylphenyl)-7-morpholino-9H-carbazole-1-carboxamide (20 mg, 0.034 mmol), morpholine (0.05 mL, 0.574 mmol), sodium triacetoxyborohydride (100 mg, 0.472 mmol) were mixed with THF (5 mL) and CH2Cl2 (2 mL) in a sealed microwave vial. The mixture was stirred for 3 hr at r.t. The mixture was concentrated and purified using preparative HPLC to give titled product. MS (ESI) m/z 485.25 (M+H)+. 1H NMR (DMSO-d6) δ ppm 11.10 (s, 1H), 8.44 (s, 1H), 8.28 (s, 1H), 8.13 (s, 1H), 8.04 (d, 1H, J=8.6), 7.67 (s, 1H), 7.62 (d, 1H, J=8.0), 7.47(s, 1H), 7.33 (d, 1H, J=7.6), 7.24 (s, 1H), 6.93 (dd, 1H, J=8.6, 1.9), 3.8 (t, 4H, J=4.7), 3.58 (bs, 4H), 3.49 (s, 2H). 3.19 (t, 4H, J=4.6), 2.45 (s, 3H), 2.4 (bs, 4H).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified

Sources & evidence

ORD record
ord-66f5b877a2bf4b7097330d0a7a0fad9c
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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