Sodium borohydride → HCID 58465063, compound

HRID 1185400Notes

Reaction equation

HRID 1185400 reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]2[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=2[F:14])=[N:4][C:3]=1[C:15]([NH:17][C:18]1[CH:19]=[N:20][N:21]([CH3:30])[C:22]=1[CH:23]1[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]1)=[O:16].[BH4-].[Na+]>CO>[NH2:1][C:2]1[S:6][C:5]([C:7]2[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=2[F:14])=[N:4][C:3]=1[C:15]([NH:17][C:18]1[CH:19]=[N:20][N:21]([CH3:30])[C:22]=1[CH:23]1[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25][CH2:24]1)=[O:16]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67437327HCID 67437327, compound

Product 1

HCID 58465063HCID 58465063, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Amino-2-(2,6-difluorophenyl)-N-(1-methyl-5-(4-oxocyclohexyl)-1H-pyrazol-4-yl)thiazole-4-carboxamide (57 mg, 0.13 mmol), prepared according to the procedures provided in Example 347, was dissolved in methanol (2 mL). Sodium borohydride (15.1 mg, 0.40 mmol) was added. The mixture was stirred at RT for 1 h, quenched with sat. NaHCO3 and extracted with ethyl acetate three times. Combined organic layers were concentrated and purified via reverse phase HPLC to give 361. 1H NMR (400 MHz, DMSO) δ 8.69 (s, 1H), 7.61-7.48 (m, 2H), 7.46 (s, 2H), 7.26 (dd, J=14.5, 5.8 Hz, 2H), 4.57 (d, J=4.4 Hz, 1H), 3.76 (s, 3H), 3.50-3.34 (m, 1H), 3.02 (td, J=6.6, 4.0 Hz, 1H), 2.84-2.60 (m, 1H), 1.91 (d, J=9.9 Hz, 2H), 1.84-1.59 (m, 5H), 1.37-1.17 (m, 2H). MS (ESI) m/z: 434.2 [M+H+].

Workup

  1. customprovided in Example 347
  2. customquenched with sat. NaHCO3
  3. extractionextracted with ethyl acetate three times
  4. concentrationCombined organic layers were concentrated
  5. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-a2d479748c864a05a220c51c17a18db7
Source dataset
uspto-grants-2014_03
Patent number
US08669361B2

Reaction notes

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