tert-Butyl 4-(3-bromobenzene-1-sulfonyl)piperazine-1-carboxylate → HCID 59244286, compound

HRID 912248Notes

Reaction equation

HRID 912248 reaction equation
C(OC(N1CCN(S(C2C=CC=C(Br)C=2)(=O)=O)CC1)=O)(C)(C)C.C(OC([N:31]1[CH2:36][CH2:35][N:34]([S:37]([C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([N:46]3[C:50]4[N:51]=[C:52]([N:80]5[CH2:85][CH2:84][O:83][CH2:82][CH2:81]5)[N:53]=[C:54]([C:55]5[CH:56]=[N:57][C:58]([N:61](CC6C=CC(OC)=CC=6)CC6C=CC(OC)=CC=6)=[N:59][CH:60]=5)[C:49]=4[CH2:48][CH2:47]3)[CH:41]=2)(=[O:39])=[O:38])[CH2:33][CH2:32]1)=O)(C)(C)C>>[N:80]1([C:52]2[N:53]=[C:54]([C:55]3[CH:60]=[N:59][C:58]([NH2:61])=[N:57][CH:56]=3)[C:49]3[CH2:48][CH2:47][N:46]([C:42]4[CH:43]=[CH:44][CH:45]=[C:40]([S:37]([N:34]5[CH2:35][CH2:36][NH:31][CH2:32][CH2:33]5)(=[O:39])=[O:38])[CH:41]=4)[C:50]=3[N:51]=2)[CH2:85][CH2:84][O:83][CH2:82][CH2:81]1

Participants

3

Reactant 2

HCID 45588490tert-Butyl 4-(3-bromobenzene-1-sulfonyl)piperazine-1-carboxylateHCID 67385372HCID 67385372, compound

Product 1

HCID 59244286HCID 59244286, compoundYield 33%

Procedure

From 4-(3-bromo-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester (prepared from 3-bromobenzenesulfonyl chloride and piperazine-1-carboxylic acid tert-butyl ester, 83 mg) instead of 1-(3-bromo-benzenesulfonyl)-4-ethyl-piperazine in Example 1-D-96, a crude product of 4-[3-(4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidin-7-yl)-benzenesulfonyl]-piperazine-1-carboxylic acid tert-butyl ester was obtained, and then the PMB groups and BOC group were removed according to the above Deprotection method 1, to obtain the desired compound (D-132) as a yellow powder (32 mg, 33%).

Workup

  1. customthe PMB groups and BOC group were removed

Sources & evidence

ORD record
ord-04a6efaf361c479d97e3060254b8b21a
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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