N-Methylethylenediamine → HCID 11271631, compound

HRID 1271002Notes

Reaction equation

[CH2:1]([N:3]([CH2:35][CH3:36])[CH2:4][CH2:5][NH:6][C:7](=[O:34])/[CH:8]=[CH:9]/[C@@H:10]([NH:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:24][CH:23]=1)=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:2].CNCCN>>[N:3]1([CH2:4][CH2:5][NH:6][C:7](=[O:34])/[CH:8]=[CH:9]/[C@@H:10]([NH:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:24][CH:23]=2)=[O:20])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:1][CH2:2][CH2:36][CH2:35]1

Participants

Reactant 2

HCID 8014N-Methylethylenediamine

HCID 11409113HCID 11409113, compound

Product 1

HCID 11271631HCID 11271631, compound

Procedure

Prepared as in Example 18, step B, from (E)-(S)-4-(3-biphenyl-4-yl-ureido)-5-phenyl-pent-2-enoic acid (Example 19, step A), substituting 2-pyrrolidin-1-yl-ethylamine for N′-methyl-ethane-1,2-diamine. MS (electrospray): mass calculated for C30H3N4O2, 482.27; m/z found, 483.3 [M+H]+, 505.2 [M+Na]+, 987.5 [2M+H]+. 1H NMR (400 MHz, CDCl3): 7.99 (s, 1H), 7.53 (d, J=7.4 Hz, 2H), 7.49–7.37 (m, 7H), 7.32–7.20 (m, 5H), 6.80 (dd, J=15.3, 5.1 Hz, 1H), 5.97–5.93 (m, 2H), 4.89–4.83 (m, 1H), 4.51–4.45 (m, 1H), 3.63–3.55 (m, 1H), 3.28–3.21 (m, 1H), 2.95 (dd, J=13.7, 7.3 Hz, 1H), 2.87 (dd, J=13.7, 7.3 Hz, 1H), 2.72–2.65 (m, 2H), 2.53–2.45 (m, 4H), 1.78–1.69 (m, 4H).

Workup

customPrepared as in Example 18, step B

Sources & evidence

ORD record: ord-32c2b823138d4d39abbd6fdaddc31a4d
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202269B2

Reaction notes

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