Acetic Acid → HCID 58015859, compound

HRID 2189320Notes

Reaction equation

HRID 2189320 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[N:18]=[CH:19][C:20]4[CH:25]=[C:24]([CH:26]=O)[N:23]([CH:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[C:21]=4[N:22]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH2:33]([NH2:39])[C:34]1[O:38][CH:37]=[CH:36][CH:35]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C>C1COCC1>[CH2:29]([CH:28]([N:23]1[C:21]2[N:22]=[C:17]([NH:16][C:13]3[CH:12]=[CH:11][C:10]([N:7]4[CH2:6][CH2:5][N:4]([C:1](=[O:3])[CH3:2])[CH2:9][CH2:8]4)=[CH:15][CH:14]=3)[N:18]=[CH:19][C:20]=2[CH:25]=[C:24]1[CH2:26][NH:39][CH2:33][C:34]1[O:38][CH:37]=[CH:36][CH:35]=1)[CH2:31][CH3:32])[CH3:30]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3438FurfurylamineHCID 5049666Sodium triacetoxyborohydrideHCID 23624284HCID 23624284, compound

Product 1

HCID 58015859HCID 58015859, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[4-(4-acetyl-piperazin-1-yl)-phenylamino]-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carbaldehyde (30 mg, 0.07 mmol) in THF (1 mL) is added furfurylamine (0.03 mL, 0.35 mmol), NaBH(OAc)3 (45 mg, 0.21 mmol), and acetic acid (1 mL). The reaction mixture is stirred for 16 h and concentrated in vacuo. The residue is purified by preparative HPLC to give 20 mg of 1-{4-[4-(7-(1-ethyl-propyl)-6-{[(furan-2-ylmethyl)-amino]-methyl}-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-phenyl]-piperazin-1-yl}-ethanone as a pale yellow solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-59211ad29cde4948965fccb63df5f049
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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