tert-butyl N-(4-aminobutyl)carbamate → N-(4-Amino-butyl)-3-(9-chloro-6-oxo-6,7-dihydro-5H-benzo[b]pyrimido[4,5-d]azepin-2-ylamino)-benzamide

HRID 2373423Notes

Reaction equation

HRID 2373423 reaction equation
ClC1C=CC2C3N=C(NC4C=C(C=CC=4)C(O)=O)N=CC=3CC(=O)NC=2C=1.NCCCCNC(=O)OC(C)(C)C.C(OC(=O)[NH:47][CH2:48][CH2:49][CH2:50][CH2:51][NH:52][C:53](=[O:78])[C:54]1[CH:59]=[CH:58][CH:57]=[C:56]([NH:60][C:61]2[N:62]=[CH:63][C:64]3[CH2:70][C:69](=[O:71])[NH:68][C:67]4[CH:72]=[C:73]([Cl:76])[CH:74]=[CH:75][C:66]=4[C:65]=3[N:77]=2)[CH:55]=1)(C)(C)C>>[NH2:47][CH2:48][CH2:49][CH2:50][CH2:51][NH:52][C:53](=[O:78])[C:54]1[CH:59]=[CH:58][CH:57]=[C:56]([NH:60][C:61]2[N:62]=[CH:63][C:64]3[CH2:70][C:69](=[O:71])[NH:68][C:67]4[CH:72]=[C:73]([Cl:76])[CH:74]=[CH:75][C:66]=4[C:65]=3[N:77]=2)[CH:55]=1

Participants

4

Reactant 3

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 56946586HCID 56946586, compoundHCID 66934713{4-[3-(9-chloro-6-oxo-6,7-dihydro-5H-benzo[b]pyrimido[4,5-d]azepin-2-ylamino)-benzoylamino]-butyl}-carbamic acid tert-butyl ester

Product 1

HCID 59851361N-(4-Amino-butyl)-3-(9-chloro-6-oxo-6,7-dihydro-5H-benzo[b]pyrimido[4,5-d]azepin-2-ylamino)-benzamide

Procedure

In a manner similar to Method N, 3-(9-chloro-6-oxo-6,7-dihydro-5H-benzo[b]pyrimido[4,5-d]azepin-2-ylamino)-benzoic acid (I-62-a) and tert-butyl 4-aminobutylcarbamate were converted to {4-[3-(9-chloro-6-oxo-6,7-dihydro-5H-benzo[b]pyrimido[4,5-d]azepin-2-ylamino)-benzoylamino]-butyl}-carbamic acid tert-butyl ester. Subsequent deprotection (Method K) and purification by C-18 RP LC-MS chromatography afforded I-64 (10%): HRMS Calcd. for C23H23ClN6O2: 451.1649, Found 451.1668.

Workup

  1. customSubsequent deprotection (Method K) and purification by C-18 RP LC-MS chromatography
  2. customafforded I-64 (10%)

Sources & evidence

ORD record
ord-067f8a65691e4bf9b250537d024a3a05
Source dataset
uspto-grants-2008_12
Patent number
US07459448B2

Reaction notes

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