Benzeneacetic acid, 4-ethoxy- → methyl [1-(cyclopropylmethyl)-2-[(4-ethoxyphenyl)methyl]-1H-benzimidazol-5-yl]carbamate

HRID 1796489Notes

Reaction equation

HRID 1796489 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:13][C:14](=[O:17])[O:15][CH3:16])[CH:5]=[CH:6][C:7]=1[NH:8][CH2:9][CH:10]1[CH2:12][CH2:11]1.CCN(C(C)C)C(C)C.[CH2:27]([O:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37](O)=O)=[CH:32][CH:31]=1)[CH3:28].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[CH3:16][O:15][C:14](=[O:17])[NH:13][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([CH2:9][CH:10]3[CH2:12][CH2:11]3)[C:37]([CH2:36][C:33]3[CH:34]=[CH:35][C:30]([O:29][CH2:27][CH3:28])=[CH:31][CH:32]=3)=[N:1][C:2]=2[CH:3]=1

Participants

5

Reactant 4

HCID 78631Benzeneacetic acid, 4-ethoxy-HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22181334Methyl 3-amino-4-[(cyclopropylmethyl)amino]-phenylcarbamate

Product 1

HCID 86605606methyl [1-(cyclopropylmethyl)-2-[(4-ethoxyphenyl)methyl]-1H-benzimidazol-5-yl]carbamate

Procedure

Following general procedure 13B: Methyl 3-amino-4-[(cyclopropylmethyl)amino]-phenylcarbamate (4.0 g, 17.0 mmol), DIPEA (5 mL), 4-ethoxyphenylacetic acid (3.06 g, 17.0 mmol) and HATU (7.10 g, 18.7 mmol) were combined. The desired product (3.34 g, 52%) precipitated out of the reaction mixture. 1HNMR (CDCl3): δ 7.65 (d, J=2.0 Hz, 1H), 7.37 (br., 1H), 7.26 (d, J=4 Hz), 7.12 (d, J=9.0 Hz, 2H), 6.81 (d, J=9.0 Hz, 2H), 6.74 (br., 1H), 4.25 (s, 2H), 3.98 (q, J=7.4 Hz, 2H), 3.87 (d, J=7.2 Hz, 2H), 3.79 (s, 3H), 1.38 (t, J=7.4 Hz, 3H), 1.05–0.97 (m, 1H), 0.52–0.47 (m, 2H), 0.25–0.20 (m, 2H). MS (ESI) (M+H)+=380.

Workup

  1. customThe desired product (3.34 g, 52%) precipitated out of the reaction mixture

Sources & evidence

ORD record
ord-64f2c01bf79246b3915cb9d412d50861
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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