Acetic Acid → HCID 67219251, compound

HRID 916762Notes

Reaction equation

HRID 916762 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH:4]=O.[NH2:11][C:12]1[C:13]2[C:20]([C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([NH2:29])[CH:24]=3)=[O:22])=[CH:19][N:18]([CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[C:14]=2[N:15]=[CH:16][N:17]=1.CC(O)=O.[BH3-]C#N.[Na+]>CO>[NH2:11][C:12]1[C:13]2[C:20]([C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([NH:29][CH2:4][C:3]4[CH:6]=[C:7]([F:10])[CH:8]=[CH:9][C:2]=4[F:1])[CH:24]=3)=[O:22])=[CH:19][N:18]([CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34]3)[C:14]=2[N:15]=[CH:16][N:17]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1376632,5-DifluorobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 11859044(4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-amino-phenyl)methanone

Product 1

HCID 67219251HCID 67219251, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,5-difluorobenzaldehyde (88.1 mg, 0.62 mmol) was added to a solution of (4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-amino-phenyl)-methanone (100 mg, 0.31 mmol) and AcOH (18.6 mg, 0.31 mmol) in MeOH (10 mL). After 5 min NaCNBH3 was added. After 3 h the reaction was quenched with 1N NaOH. The aqueous layer was extracted with EtOAc (2×). The combined organic layers were washed with water, dried over MgSO4, and concentrated. Purification by flash column chromatography (CH2Cl2/MeOH 98:2) afforded the title compound as a white solid (80 mg, 58%). MS: 448.1 (MH+); HPLC Rf: 6.59 min. (HPLC method 4).

Workup

  1. customAfter 3 h the reaction was quenched with 1N NaOH
  2. extractionThe aqueous layer was extracted with EtOAc (2×)
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customPurification by flash column chromatography (CH2Cl2/MeOH 98:2)

Sources & evidence

ORD record
ord-5d2dd7574ebc4aaa8f7a5cd5312f665f
Source dataset
uspto-grants-2007_09
Patent number
US07271262B2

Reaction notes

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