Methyl iodide → HCID 68834385, compound

HRID 2113314Notes

Reaction equation

HRID 2113314 reaction equation
COC(=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11](=[O:38])[CH2:12][N:13]2[N:19]=[C:18]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:17]3[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=3[N:15]([CH2:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[C:14]2=[O:37])[CH:5]=1.[C:40]([O:44][C:45](=[O:59])[N:46]([C:52]1C=CC=[C:54](N)[CH:53]=1)CCOCC)([CH3:43])([CH3:42])[CH3:41].C(OC(=O)N(C1C=CC=C(N)C=1)C)(C)(C)C.BrCCOCC.IC.COC(=O)C1C=CC=C(N)C=1>>[C:40]([O:44][C:45](=[O:59])[N:46]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11](=[O:38])[CH2:12][N:13]2[N:19]=[C:18]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:17]3[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=3[N:15]([CH2:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:33])[CH3:34])[C:14]2=[O:37])[CH:5]=1)[CH2:52][CH2:53][CH3:54])([CH3:43])([CH3:42])[CH3:41]

Participants

7

Reactant 6

HCID 6328Methyl iodideHCID 611412-Bromoethyl ethyl etherHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 102181623-{2-[5-Cyclohexyl-1-(3,3-dimethyl-2-oxo-butyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl]-acetylamino}-benzoic acid methyl esterHCID 11492276tert-butyl N-(3-aminophenyl)-N-methylcarbamateHCID 11594336HCID 11594336, compound

Product 1

HCID 68834385HCID 68834385, compound

Procedure

The title compound was obtained as the hydrochloride salt by the method used in the preparation of 3-{2-[5-cyclohexyl-1-(3,3-dimethyl-2-oxo-butyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl]-acetylamino}-benzoic acid methyl ester (Example 1), except that (3-amino-phenyl)-2-ethoxyethyl-carbamic acid tert-butyl ester (obtained using the method employed in the preparation of (3-amino-phenyl)-methyl-carbamic acid tert-butyl ester (Example 3, step c) except that 2-bromoethyl-ethyl ether was used in step b instead of iodomethane) was used instead of 3-amino-benzoic acid methyl ester in step e, followed by reaction of the product obtained, in place of (3-{2-[5-cyclohexyl-1-(3,3-dimethyl-2-oxo-butyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl]-acetylamino}-phenyl)-propyl-carbamic acid tert-butyl ester (Example 41, step a) according to the method of Example 41 step b. 1H NMR (CDCl3) 8.45 (1H, s), 7.61 (1H, s), 7.56-7.47 (2H, m), 7.36 (4H, m), 7.03 (1H, d), 4.70 (2H, dd), 4.26 (2H, dd), 3.73 (2H, br s), 3.51 (4H, m), 2.82 (1H, br s), 2.05-1.65 (6H, m), 1.30-1.17 (16H, m). Found: C, 63.90; H, 7.66; N, 11.58%; C32H43N5O4.HCl.0.25H2O requires: C, 63.77; H, 7.44; N, 11.62%.

Workup

  1. customobtained
  2. customfollowed by reaction of the product

Sources & evidence

ORD record
ord-af2cdcd15ffa4ed2b3c9becb0c2ba994
Source dataset
uspto-grants-2009_04
Patent number
US07524837B2

Reaction notes

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