Triethylamine → HCID 11376691, compound

HRID 736090Notes

Reaction equation

C(O[C:4]([C:6]1[C:12]2NC3C=CC=CC=3[C:11]=2CCNC=1)=O)C.[CH2:20]([O:22][C:23]([C:25]1[C:31]2[NH:32][C:33]3[CH:34]=[C:35](O)[CH:36]=[CH:37][C:38]=3[C:30]=2[C:29]([CH3:41])([CH3:40])[CH2:28][N:27]([C:42](=[O:51])[C:43]2[CH:48]=[CH:47][C:46]([F:49])=[C:45](F)[CH:44]=2)[CH:26]=1)=[O:24])[CH3:21].[CH2:52]([N:54](CC)[CH2:55]C)C.[CH2:59]([N:62]=[C:63]=[O:64])[CH2:60][CH3:61]>C(Cl)Cl>[CH2:20]([O:22][C:23]([C:25]1[C:31]2[NH:32][C:33]3[CH:34]=[CH:35][C:36]([N:62]([CH2:59][C:60]4[CH:11]=[CH:12][CH:6]=[CH:4][CH:61]=4)[C:63]([N:54]([CH3:55])[CH3:52])=[O:64])=[CH:37][C:38]=3[C:30]=2[C:29]([CH3:41])([CH3:40])[CH2:28][N:27]([C:42](=[O:51])[C:43]2[CH:44]=[CH:45][C:46]([F:49])=[CH:47][CH:48]=2)[CH:26]=1)=[O:24])[CH3:21]

Participants

Conditions

Temperature: 60 °C

Procedure

To prepare 3-(3,4-difluoro-benzoyl)-1,1-dimethyl-8-propylcarbamoyloxy)-1,2,3,6-tetrahydro-azepino[4,5-b]indole-5-carboxylic acid ethyl ester, a mixture of 3-(3,4-difluoro-benzoyl)-8-hydroxy-1,1-dimethyl-1,2,3,6-tetrahydro-azepino[4,5-b]-indole-5-carboxylic acid ethyl ester (45 mg, 0.1 mmol), triethylamine (0.1 mL), and propylisocyanate (0.2 mL) in dry DCM (5 mL) was refluxed at 60° C. for 20 hours. The solvent was removed in vacuo, and the residue was purified by preparative reverse-phase HPLC to give the title compound, which was then acylated in the manner described in Example 2A; 1HNMR (CDCl3): δ 10.62 (1H, s), 7.76-7.73 (2H, m), 7.52-7.47 (1H, m), 7.36-7.31 (1H, m), 7.24-7.19 (1H, m), 7.16 (1H, d), 6.86 (1H, m), 5.04 (1H, t), 4.26 (2H, q), 4.09 (2H, brs), 3.25 (2H, q), 1.66-1.54 (8H, m), 1.25 (3H, t), 0.99 (3H, t). MS (ES): 526 (MH+).

Workup

customThe solvent was removed in vacuo
customthe residue was purified by preparative reverse-phase HPLC

Sources & evidence

ORD record: ord-069b2d69d5044a5aaad7afa1d1de8c8f
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595311B2

Reaction notes

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