Sodium borohydride → HCID 70984094, compound

HRID 928153Notes

Reaction equation

HRID 928153 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]([C:13]3[S:14][C:15]([C:18]4[CH:23]=[C:22]([NH:24][C:25]5[N:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][N:26]=5)[CH:21]=[C:20]([CH3:35])[CH:19]=4)=[CH:16][N:17]=3)=[O:12])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[BH4-].[Na+]>CO.C(OCC)(=O)C.O>[O:1]1[C:5]2([CH2:6][CH2:7][CH:8]([CH:11]([C:13]3[S:14][C:15]([C:18]4[CH:23]=[C:22]([NH:24][C:25]5[N:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][N:26]=5)[CH:21]=[C:20]([CH3:35])[CH:19]=4)=[CH:16][N:17]=3)[OH:12])[CH2:9][CH2:10]2)[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 70984468HCID 70984468, compound

Product 1

HCID 70984094HCID 70984094, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,4-dioxaspiro[4.5]dec-8-yl[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]methanone (Ex 1-20) (100 mg, 0.20 mmol) in methanol (5 mL) was added sodium borohydride (22.5 mg, 0.60 mmol). After one hour, water was carefully added and then diluted with ethyl acetate and water. The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography on silica gel (0-100% ethyl acetate gradient with hexanes) afforded 1,4-dioxaspiro[4.5]dec-8-yl[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]methanol. MS ESI calc'd. for C24H26F3N4O3S [M+H]+ 507. found 507. 1H NMR (500 MHz, DMSO-d6) δ 10.24 (s, 1H), 8.83 (d, J=4.9, 1H), 7.97-7.94 (m, 2H), 7.45 (s, 1H), 7.27 (d, J=4.9, 1H), 7.15 (s, 1H), 6.18 (d, J=5.1, 1H), 4.61 (t, J=5.1, 1H), 3.80 (s, 4H), 2.30 (s, 3H), 1.84-1.72 (m, 1H), 1.71-1.61 (m, 2H), 1.61-1.51 (m, 2H), 1.52-1.28 (m, 4H). rhSyk=++.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-771dfbf4ecea4025bed6d0245bfba2ae
Source dataset
uspto-grants-2016_03
Patent number
US09290490B2

Reaction notes

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