tert-butyl N-(prop-2-yn-1-yl)carbamate → HCID 59851457, compound

HRID 545037Notes

Reaction equation

HRID 545037 reaction equation
ClC1C=CC2C3N=C(NC4C=CC=C(I)C=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][CH:50]=[C:49]([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:48]=1)(C)(C)C>>[NH2:43][CH2:44][C:45]#[C:46][C:47]1[CH:48]=[C:49]([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:50]=[CH:51][CH:52]=1

Participants

4

Reactant 3

HCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 598512839-Chloro-2-(3-iodo-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-oneHCID 66934682HCID 66934682, compound

Product 1

HCID 59851457HCID 59851457, compound

Procedure

In a manner similar to that described for Method O, 9-chloro-2-(3-iodo-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one (I-58) and tert-butyl prop-2-ynylcarbamate was converted to {3-[3-(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 subsequently deprotected according to Method Kto give I-67 (62%): HRMS Calcd. for C21H16ClN5O: 390.1121, Found 390.1117.

Workup

  1. customgive I-67 (62%)

Sources & evidence

ORD record
ord-e1e382f1f31344a08be3df4342388e6a
Source dataset
uspto-grants-2011_05
Patent number
US07935694B2

Reaction notes

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