L-Alanine-(R)-2-[5-(3-ethanesulfonyl-phenyl)-3-methyl-9H-dipyrido[2,3-b;4',3'-d]pyrrol-8-yloxy]-1-methyl-ethyl ester → (S)-2-(5-(3-(ethylsulfonyl)phenyl)-3-methyl-9H-pyrido[2,3-b]indol-8-yloxy)ethyl2-aminopropanoate

HRID 1642578Notes

Reaction equation

HRID 1642578 reaction equation
[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([C:12]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][OH:24])=[C:17]3[C:13]=2[C:14]2[CH:28]=[C:27]([CH3:29])[CH:26]=[N:25][C:15]=2[NH:16]3)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4])[CH3:2].C(S(C1C=C(C2[C:46]3C4C=C(C)C=NC=4[NH:49][C:45]=3[C:44]([O:55]C[C@H](OC(=O)[C@H](C)N)C)=NC=2)C=CC=1)(=O)=O)C>>[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([C:12]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][O:24][C:44](=[O:55])[C@@H:45]([NH2:49])[CH3:46])=[C:17]3[C:13]=2[C:14]2[CH:28]=[C:27]([CH3:29])[CH:26]=[N:25][C:15]=2[NH:16]3)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4])[CH3:2]

Participants

3

Reactant 2

HCID 16123544L-Alanine-(R)-2-[5-(3-ethanesulfonyl-phenyl)-3-methyl-9H-dipyrido[2,3-b;4',3'-d]pyrrol-8-yloxy]-1-methyl-ethyl esterHCID 588801692-(5-(3-(ethylsulfonyl)phenyl)-3-methyl-9H-pyrido[2,3-b]indol-8-yloxy)ethanol

Product 1

HCID 58880193(S)-2-(5-(3-(ethylsulfonyl)phenyl)-3-methyl-9H-pyrido[2,3-b]indol-8-yloxy)ethyl2-aminopropanoate

Procedure

The title compound was prepared from Compound 215 by using an analogous procedure to that outlined in the preparation of Compound 64. 1H NMR (400 MHz, DMSO) δ ppm 1.18 (t, J=7.33 Hz, 3 H) 1.40 (d, J=7.33 Hz, 3 H) 2.27 (s, 3 H) 3.42 (q, J=7.33 Hz, 2 H) 4.20 (d, J=5.05 Hz, 1 H) 4.53 (t, J=4.42 Hz, 2 H) 4.58-4.69 (m, 2 H) 7.12 (d, J=8.08 Hz, 1 H) 7.23 (d, J=8.08 Hz, 1 H) 7.55 (s, 1 H) 7.87 (t, J=7.83 Hz, 1 H) 8.00 (dd, J=12.63, 7.58 Hz, 2 H) 8.08 (s, 1 H) 8.29 (s, 1 H) 8.33 (br. s., 2 H) 11.95 (s, 1 H) [M+H] calc'd for C25H27N3O5S, 482; found, 482.

Sources & evidence

ORD record
ord-62aa61dd877f4e9fb7454c0ce64575aa
Source dataset
uspto-grants-2012_02
Patent number
US08119655B2

Reaction notes

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