Sodium triacetoxyborohydride → HCID 44819482, compound

HRID 1483134Notes

Reaction equation

HRID 1483134 reaction equation
[CH3:1][N:2]([CH3:32])[C:3]([C:5]1[N:26]([CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[C:8]2[N:9]=[C:10]([NH:13][C:14]3[N:19]=[CH:18][C:17]([CH:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].ClCCl.[CH3:50][C:51]([CH3:53])=O>C(O)(=O)C>[CH3:1][N:2]([CH3:32])[C:3]([C:5]1[N:26]([CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[C:8]2[N:9]=[C:10]([NH:13][C:14]3[N:19]=[CH:18][C:17]([CH:20]4[CH2:25][CH2:24][N:23]([CH:51]([CH3:53])[CH3:50])[CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 21584124Propan-2-one--dichloromethane (1/1)HCID 44819303HCID 44819303, compound

Product 1

HCID 44819482HCID 44819482, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

To a suspension of 7-cyclopentyl-2-(1′,2′,3′,4′,5′,6′-hexahydro-[3,4′]bipyridinyl-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (100 mg, 0.23 mmol) in dichloromethane/acetone is added NaBH(OAc)3 (488 mg, 2.3 mmol) followed by 3 drops of glacial acetic acid. After reaction is completed and concentrated. Diluted with 100 mL of H2O and basified to pH12 with 50% NaOH solution dropwise (2 mL). Extracted with dichloromethane (3×100 mL) and concentrated to give 7-cyclopentyl-2-(1′-isopropyl-1′,2′,3′,4′,5′,6′-hexahydro-[3,4′]bipyridinyl-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (65 mg, 60%). MS (ESI) m/z 476.3 (M+H)|

Workup

  1. customAfter reaction
  2. concentrationconcentrated
  3. additionDiluted with 100 mL of H2O and basified to pH12 with 50% NaOH solution dropwise (2 mL)
  4. extractionExtracted with dichloromethane (3×100 mL)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4d89f4b1c5564ae990c2bb2b8fbd5936
Source dataset
uspto-grants-2016_08
Patent number
US09416136B2

Reaction notes

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