Hydrochloric Acid → 2-chloro-5-fluoro-6-hydrazino-N-(4-methyl-1-piperazinyl)-N-(1,3-thiazol-2-ylmethyl)-4-pyrimidinamine

HRID 1366705Notes

Reaction equation

HRID 1366705 reaction equation
CC(OC([N:8](C(OC(C)(C)C)=O)[N:9]([C:17]1[C:22]([F:23])=[C:21]([N:24]([N:31]2[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]2)[CH2:25][C:26]2[S:27][CH:28]=[CH:29][N:30]=2)[N:20]=[C:19]([Cl:38])[N:18]=1)C(OC(C)(C)C)=O)=O)(C)C.Cl>C(Cl)Cl>[Cl:38][C:19]1[N:20]=[C:21]([N:24]([N:31]2[CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH2:36]2)[CH2:25][C:26]2[S:27][CH:28]=[CH:29][N:30]=2)[C:22]([F:23])=[C:17]([NH:9][NH2:8])[N:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86637031Tris(1,1-dimethylethyl) 2-{2-chloro-5-fluoro-6-[(4-methyl-1-piperazinyl)(1,3-thiazol-2-ylmethyl)amino]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate

Product 1

HCID 866370322-chloro-5-fluoro-6-hydrazino-N-(4-methyl-1-piperazinyl)-N-(1,3-thiazol-2-ylmethyl)-4-pyrimidinamineYield 151%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tris(1,1-dimethylethyl)2-{2-chloro-5-fluoro-6-[(4-methyl-1-piperazinyl)(1,3-thiazol-2-ylmethyl)amino]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate (0.2014 g, 0.299 mmol) was dissolved in DCM (20 mL) under a nitrogen atmosphere. Then 2M HCl (2.99 mL, 5.98 mmol) was added, and the reaction was stirred overnight. The reaction mixture was evaporated to provide crude 2-chloro-5-fluoro-6-hydrazino-N-(4-methyl-1-piperazinyl)-N-(1,3-thiazol-2-ylmethyl)-4-pyrimidinamine as a yellow solid (0.1683 g). LCMS: (M+H)+=373.0.

Workup

  1. customThe reaction mixture was evaporated

Sources & evidence

ORD record
ord-b748244050c144fdba9152280b01b54d
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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