5-Bromo-1-ethyl-indole-2-carboxylic acid → (S)-3-{5-[(5-Bromo-1-ethyl-1H-indole-2-carbonyl)-amino]-pyridin-2-ylamino}-pyrrolidine-1-carboxylic acid ethyl ester hydrochloride

HRID 1645355Notes

Reaction equation

HRID 1645355 reaction equation
[ClH:1].[CH2:2]([O:4][C:5]([N:7]1[CH2:11][CH2:10][C@H:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]3S[C:25]4[CH:27]=[CH:28][C:29]([Br:31])=[CH:30][C:24]=4[CH:23]=3)=[O:21])=[CH:15][N:14]=2)[CH2:8]1)=[O:6])[CH3:3].C(OC([N:37]1CC[C@H:39](NC2C=CC(N)=CN=2)[CH2:38]1)=O)C.BrC1C=C2C(=CC=1)N(CC)C(C(O)=O)=C2>>[ClH:1].[CH2:2]([O:4][C:5]([N:7]1[CH2:11][CH2:10][C@H:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]3[N:37]([CH2:38][CH3:39])[C:25]4[C:24]([CH:23]=3)=[CH:30][C:29]([Br:31])=[CH:28][CH:27]=4)=[O:21])=[CH:15][N:14]=2)[CH2:8]1)=[O:6])[CH3:3]

Participants

4

Reactant 3

HCID 529110085-Bromo-1-ethyl-indole-2-carboxylic acidHCID 59365133(S)-3-(5-amino-pyridin-2-ylamino)-pyrrolidine-1-carboxylic acid ethyl esterHCID 66772122HCID 66772122, compound

Product 1

HCID 66772560(S)-3-{5-[(5-Bromo-1-ethyl-1H-indole-2-carbonyl)-amino]-pyridin-2-ylamino}-pyrrolidine-1-carboxylic acid ethyl ester hydrochloride

Procedure

With a method similar to that used for the preparation of (S)-3-{5-[(5-bromo-benzo[b]thiophene-2-carbonyl)-amino]-pyridin-2-ylamino}-pyrrolidine-1-carboxylic acid ethyl ester hydrochloride, (S)-3-{5-[(5-bromo-1-ethyl-1,4-indole-2-carbonyl)-amino]-pyridin-2-ylamino}-pyrrolidine-1-carboxylic acid ethyl ester hydrochloride was prepared from (S)-3-(5-amino-pyridin-2-ylamino)-pyrrolidine-1-carboxylic acid ethyl ester and 5-bromo-1-ethyl-indole-2-carboxylic acid. LCMS for C23H26BrN5O3 calcd. (m/e) 499, observed 500 (M+H).

Sources & evidence

ORD record
ord-fa719a9111a34d30b69d35cb7dccccec
Source dataset
uspto-grants-2012_02
Patent number
US08124766B2

Reaction notes

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