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Acetyl chloride → HCID 178474044, compound

HRID 51587
Notes
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Reaction equation

HRID 51587 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:15]2[C:23]3[C:22]([NH2:24])=[N:21][CH:20]=[N:19][C:18]=3[N:17]([C@H:25]3[CH2:30][CH2:29][C@H:28]([N:31]4[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]4)[CH2:27][CH2:26]3)[CH:16]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:38](Cl)(=[O:40])[CH3:39]>N1C=CC=CC=1.ClCCl>[C:9]([OH:40])(=[O:8])[CH3:14].[NH2:24][C:22]1[C:23]2[C:15]([C:4]3[CH:5]=[CH:6][C:7]([O:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)=[C:2]([NH:1][C:38](=[O:40])[CH3:39])[CH:3]=3)=[CH:16][N:17]([C@H:25]3[CH2:30][CH2:29][C@H:28]([N:31]4[CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH2:36]4)[CH2:27][CH2:26]3)[C:18]=2[N:19]=[CH:20][N:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 178480942HCID 178480942, compound

Product 1

HCID 178474044HCID 178474044, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of trans-5-(3-amino-4-phenoxyphenyl)-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (120 mg, 0.241 mmol) in pyridine (2 mL) and dichloromethane (2 mL) was cooled to 0° C. then treatd with acetyl chloride (25 mg, 0.3 mmol). The mixture was warmed to ambient temperature for one hour then the solvents were removed under reduced pressure and the residue purified by preparative RP-HPLC to give trans-N1-(5-{4-amino-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}-2-phenoxyphenyl)acetamide acetate (45 mg, 35%): 1H NMR (DMSO-d6, 400 MHz) δ 9.67 (bs, 1H), 8.11(s, 1H), 8.00(s, 1H), 7.40(t, 3H), 7.17(m, 2H), 7.05(d, 2H), 6.95(d, 1H), 6.30(bs, 2H), 4.55(m, 1H), 2.2-2.6(m, 9H), 2.14(s, 3H), 2.04(s, 3H), 1.8-2.0(m, 6H), 1.89(s, 3H), 1.44(m, 2H); MS MH+540.5; RP-HPLC (Hypersil HS, 5 μm, 1000 A, 4.6×250 mm; 5%-50% acetonitrile—0.05 M ammonium acetate over 25 min, 1 ml/min) tr 20.37 min.

Workup

  1. temperatureThe mixture was warmed to ambient temperature for one hour
  2. customthe solvents were removed under reduced pressure
  3. customthe residue purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-c4eb268dcbfd4bfeba0d504d7521a8d3
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06713474B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes