tert-butyl N-(prop-2-yn-1-yl)carbamate → 2-[4-(3-Amino-prop-1-ynyl)-phenylamino]-9-chloro-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

HRID 545030Notes

Reaction equation

HRID 545030 reaction equation
ClC1C=CC2C3N=C(NC4C=CC(I)=CC=4)N=CC=3CC(=O)NC=2C=1.C(NC(=O)OC(C)(C)C)C#C.C(OC(=O)[NH:43][CH2:44][C:45]#[C:46][C:47]1[CH:52]=[CH:51][C:50]([NH:53][C:54]2[N:55]=[CH:56][C:57]3[CH2:63][C:62](=[O:64])[NH:61][C:60]4[CH:65]=[C:66]([Cl:69])[CH:67]=[CH:68][C:59]=4[C:58]=3[N:70]=2)=[CH:49][CH:48]=1)(C)(C)C>>[NH2:43][CH2:44][C:45]#[C:46][C:47]1[CH:52]=[CH:51][C:50]([NH:53][C:54]2[N:55]=[CH:56][C:57]3[CH2:63][C:62](=[O:64])[NH:61][C:60]4[CH:65]=[C:66]([Cl:69])[CH:67]=[CH:68][C:59]=4[C:58]=3[N:70]=2)=[CH:49][CH:48]=1

Participants

4

Reactant 3

HCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 569465889-Chloro-2-(4-iodo-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-oneHCID 67198932{3-[4-(9-chloro-6-oxo-6,7-dihydro-5H-benzo[b]pyrimido[4,5-d]azepin-2-ylamino)-phenyl]-prop-2-ynyl}-carbamic acid tert-butyl ester

Product 1

HCID 598514512-[4-(3-Amino-prop-1-ynyl)-phenylamino]-9-chloro-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 tert-butyl prop-2-ynylcarbamate were converted to {3-[4-(9-chloro-6-oxo-6,7-dihydro-5H-benzo[b]pyrimido[4,5-d]azepin-2-ylamino)-phenyl]-prop-2-ynyl}-carbamic acid tert-butyl ester, which was deprotected according to Method K to give I-46 (29%): HRMS Calcd. for C21H16ClN5O: 390.1121, Found 390.1120.

Workup

  1. customto give I-46 (29%)

Sources & evidence

ORD record
ord-eafe4f43b8054a6b9779f29bf5572570
Source dataset
uspto-grants-2011_05
Patent number
US07935694B2

Reaction notes

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