Terephthaloyl chloride → HCID 90221050, compound

HRID 1481932Notes

Reaction equation

[C:1](Cl)(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:8])=[O:7])=[CH:4][CH:3]=1.C(OC(=O)[N:19]([CH3:49])[C@H:20]([C:22](=[O:48])[NH:23][C@@H:24]1[C:30](=[O:31])[N:29]([CH2:32][C:33]2[C:42]3[C:37](=CC=C[CH:41]=3)[CH:36]=[CH:35][C:34]=2[CH3:43])[C:28]2[CH:44]=[CH:45][CH:46]=[CH:47][C:27]=2[NH:26][CH2:25]1)[CH3:21])(C)(C)C>>[ClH:8].[ClH:8].[CH3:49][NH:19][C@@H:20]([CH3:21])[C:22]([NH:23][C@H:24]1[CH2:25][N:26]([C:1](=[O:11])[C:2]2[CH:10]=[CH:9][C:5]([C:6]([N:26]3[C:27]4[CH:47]=[CH:46][CH:45]=[CH:44][C:28]=4[N:29]([CH2:32][C:33]4[C:42]5[C:37](=[CH:1][CH:2]=[CH:3][CH:41]=5)[CH:36]=[CH:35][C:34]=4[CH3:43])[C:30](=[O:31])[C@@H:24]([NH:23][C:22](=[O:48])[C@@H:20]([NH:19][CH3:49])[CH3:21])[CH2:25]3)=[O:7])=[CH:4][CH:3]=2)[C:27]2[CH:47]=[CH:46][CH:45]=[CH:44][C:28]=2[N:29]([CH2:32][C:33]2[C:42]3[C:37](=[CH:4][CH:5]=[CH:6][CH:41]=3)[CH:36]=[CH:35][C:34]=2[CH3:43])[C:30]1=[O:31])=[O:48]

Participants

Reactant 2

HCID 7488Terephthaloyl chloride

HCID 90220886HCID 90220886, compound2×

Product 1

HCID 90221050HCID 90221050, compoundYield 32.6%

Procedure

In a similar manner to that described for Example 22, terephthaloyl chloride (60 mg, 0.296 mmol) and methyl-{(S)-1-[(S)-1-(2-methyl-naphthalen-1-ylmethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester (Intermediate 15) (305.37 mg, 0.591 mmol) were converted to the title compound (50 mg) as an off white solid. LC-MS: 963.6 (M+H).

Sources & evidence

ORD record: ord-8e3c6407e359463f963611f6d8f06c5c
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409888B2

Reaction notes

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