Triethylamine → Methyl 4-{[({10-[(4-chloro-2-methylphenoxy)acetyl]-10,11-dihydro-5H-pyrrolo[2, 1-C][1,4]benzodiazepin-3-YL}carbonyl)amino]methyl}benzoate

HRID 639280Notes

Reaction equation

HRID 639280 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[N:14]2[C:8]([CH2:9][N:10]([C:19](=[O:30])[CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[CH3:29])[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13]2)=[CH:7][CH:6]=1)=[O:4].Cl.[NH2:34][CH2:35][C:36]1[CH:45]=[CH:44][C:39]([C:40]([O:42][CH3:43])=[O:41])=[CH:38][CH:37]=1.C(N(CC)CC)C>>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:20][C:19]([N:10]2[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13][N:14]3[C:5]([C:3]([NH:34][CH2:35][C:36]4[CH:37]=[CH:38][C:39]([C:40]([O:42][CH3:43])=[O:41])=[CH:44][CH:45]=4)=[O:4])=[CH:6][CH:7]=[C:8]3[CH2:9]2)=[O:30])=[C:23]([CH3:29])[CH:24]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideHCID 160392952,2,2-Trichloro-1-{10-[(4-chloro-2-methylphenoxy)acetyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone

Product 1

HCID 16039364Methyl 4-{[({10-[(4-chloro-2-methylphenoxy)acetyl]-10,11-dihydro-5H-pyrrolo[2, 1-C][1,4]benzodiazepin-3-YL}carbonyl)amino]methyl}benzoate

Procedure

The title compound was synthesized from 2,2,2-trichloro-1-{10-[(4-chloro-2-methylphenoxy)acetyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone of Example 75 (0.3 mmol), methyl 4-(aminomethyl)benzoate hydrochloride (2.2 eq.) and triethylamine (2.4 eq.) in the manner of Example 68, m.p.165-167° C. MS [(+)ESI, m/z]: 558 [M+H]+ Anal. Calcd for C31H28CIN3O5: C, 66.72; H, 5.06; N, 7.53. Found: C, 66.46; H, 5.26; N, 7.24.

Sources & evidence

ORD record
ord-60bbf8e40f054454bec6e8ed1b987e46
Source dataset
uspto-grants-2010_04
Patent number
US07691848B2

Reaction notes

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