Trimethylsilylacetylene → 9-Chloro-2-(4-ethynyl-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

HRID 2373406Notes

Reaction equation

ClC1C=CC2C3N=C(NC4C=CC(I)=CC=4)N=CC=3CC(=O)NC=2C=1.C([Si](C)(C)C)#C.[Cl:32][C:33]1[CH:34]=[CH:35][C:36]2[C:42]3[N:43]=[C:44]([NH:47][C:48]4[CH:53]=[CH:52][C:51]([C:54]#[C:55][Si](C)(C)C)=[CH:50][CH:49]=4)[N:45]=[CH:46][C:41]=3[CH2:40][C:39](=[O:60])[NH:38][C:37]=2[CH:61]=1>>[Cl:32][C:33]1[CH:34]=[CH:35][C:36]2[C:42]3[N:43]=[C:44]([NH:47][C:48]4[CH:53]=[CH:52][C:51]([C:54]#[CH:55])=[CH:50][CH:49]=4)[N:45]=[CH:46][C:41]=3[CH2:40][C:39](=[O:60])[NH:38][C:37]=2[CH:61]=1

Participants

Reactant 3

HCID 66111Trimethylsilylacetylene

HCID 569465889-Chloro-2-(4-iodo-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

HCID 669346909-chloro-2-(4-trimethylsilanylethynyl-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

Product 1

HCID 598510369-Chloro-2-(4-ethynyl-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

Procedure

In a manner similar to that described for Method O, 9-chloro-2-(4-iodo-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one (I-36) and ethynyltrimethylsilane were converted to 9-chloro-2-(4-trimethylsilanylethynyl-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one, which was deprotected in a manner similar to I-33 to give I-45 (38%): HRMS Calcd. for C20H13ClN4O: 361.0856, Found 361.0848.

Workup

customto give I-45 (38%)

Sources & evidence

ORD record: ord-b7614f21872e4c33bfc424f8c61ceb6d
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459448B2

Reaction notes

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