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)-3-(5-(3-(ethylsulfonyl)phenyl)-3-methyl-9H-pyrido[2,3-b]indol-8-yloxy)propyl2-aminopropanoate

HRID 1882271Notes

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][CH2:24][OH:25])=[C:17]3[C:13]=2[C:14]2[CH:29]=[C:28]([CH3:30])[CH:27]=[N:26][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:47]3C4C=C(C)C=NC=4[NH:50][C:46]=3[C:45]([O:56]C[C@H](OC(=O)[C@H](C)N)C)=NC=2)C=CC=1)(=O)=O)C>>[NH2:50][C@@H:46]([CH3:47])[C:45]([O:25][CH2:24][CH2:23][CH2:22][O:21][C:18]1[CH:19]=[CH:20][C:12]([C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH:7]=2)=[C:13]2[C:17]=1[NH:16][C:15]1[N:26]=[CH:27][C:28]([CH3:30])=[CH:29][C:14]2=1)=[O:56]

Participants

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 ester

HCID 588801363-(5-(3-(ethylsulfonyl)phenyl)-3-methyl-9H-pyrido[2,3-b]indol-8-yloxy)propan-1-ol

Product 1

HCID 58880057(S)-3-(5-(3-(ethylsulfonyl)phenyl)-3-methyl-9H-pyrido[2,3-b]indol-8-yloxy)propyl2-aminopropanoate

Procedure

The title compound was prepared from Compound 216 by using an analogous procedure to that outlined in the preparation of Compound 64. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.17 (t, J=7.33 Hz, 3H) 1.39 (d, J=7.07 Hz, 3H) 2.20-2.24 (m, 2H) 2.26 (s, 3H) 4.14 (m, 1H) 4.32 (t, J=5.68 Hz, 2H) 4.56 (m., 2H) 7.08-7.11 (m, 1H) 7.12-7.16 (m, 1H) 7.55 (s, 1H) 7.85 (t, J=7.83 Hz, 1H) 7.98 (dd, J=10.23, 8.46 Hz, 2H) 8.06 (s, 1H) 8.28 (br. s., 3H) 12.07 (s, 1H); [M+H] calc'd for C26H30N3O5S, 496.2; found, 496.4.

Sources & evidence

ORD record: ord-4f0c71653f044e5b919cdb97c599e743
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318939B2

Reaction notes

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