Glycine, N-methyl-, methyl ester, hydrochloride (1:1) → Methyl 2-(1-(5-bromopyrimidin-2-yl)-N-methyl-3-(methylthio)-1H-indole-6-carboxamido)acetate

HRID 630532Notes

Reaction equation

HRID 630532 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([OH:19])=O)[CH:15]=3)[C:10]([S:20][CH3:21])=[CH:9]2)=[N:6][CH:7]=1.Cl.[CH3:23][NH:24][CH2:25][C:26]([O:28][CH3:29])=[O:27].CSC1C2C(=CC(C(N3C[C@@H]4C[C@H]3CN4C(OC(C)(C)C)=O)=O)=CC=2)N(C2N=CC(C3C=CC=CN=3)=CN=2)C=1>>[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([N:24]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH3:23])=[O:19])[CH:15]=3)[C:10]([S:20][CH3:21])=[CH:9]2)=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)HCID 1186660601-(5-Bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylic acidHCID 131735400(1S,4S)-tert-Butyl 5-(3-(methylthio)-1-(5-(pyridin-2-yl)pyrimidin-2-yl)-1H-indole-6-carbonyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Product 1

HCID 118666033Methyl 2-(1-(5-bromopyrimidin-2-yl)-N-methyl-3-(methylthio)-1H-indole-6-carboxamido)acetate

Procedure

Amide coupling of 1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylic acid (2.0 g, 5.49 mmol) with methyl 2-(methylamino)acetate hydrochloride (1.53 g, 10.9 mmol) analogously to the protocol 244c). White solid. Yield: 0.6 g (24% of theory)

Sources & evidence

ORD record
ord-1a0f47997951415f948244dcb9df5e77
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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