Chloroacetyl chloride → HCID 178508600, compound

HRID 2053007Notes

Reaction equation

HRID 2053007 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:6][C@H:5]([N:7]2[C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH2:16])[C:10]=3[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:18]=3)=[CH:8]2)[CH2:4]1.[Cl:31][CH2:32][C:33](Cl)=[O:34].C(N(CC)CC)C>C(#N)C>[NH2:16][C:15]1[C:10]2[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:18]=3)=[CH:8][N:7]([C@H:5]3[CH2:4][C@H:3]([CH2:2][NH:1][C:33](=[O:34])[CH2:32][Cl:31])[CH2:6]3)[C:11]=2[N:12]=[CH:13][N:14]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 178511295HCID 178511295, compound

Product 1

HCID 178508600HCID 178508600, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 210 mg (0.53 mmol) of trans-7-(3-aminomethyl-cyclobutyl)-5-(3-benzyloxy-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine in 10 ml of acetonitrile is added 49 μl (0.61 mmol) of chloro-acetyl chloride (Fluka, Buchs, Switzerland) and 85 μl (0.61 mmol) of triethylamine. The solution is stirred for 5 h at RT. trans-N-{3-[4-amino-5-(3-benzyloxy-phenyl)-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutylmethyl}-2-chloro-acetamide is obtained after purification of the crude mixture by medium-pressure liquid chromatography. Analytical HPLC: tR=6.94 min (Grad 2); ES-MS: m/eo=476.0.

Sources & evidence

ORD record
ord-22e5ed9520164280bdc21c026e3bb021
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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