Boc-DL-valine → HCID 178467149, compound

HRID 526216Notes

Reaction equation

HRID 526216 reaction equation
Cl.Cl.[NH2:3][CH:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([Cl:21])[N:19]=3)[N:14]=[CH:13][C:12]=2[C:22](=[O:24])[CH3:23])[CH2:6][CH2:5]1.[C:25]([O:29][C:30]([NH:32][CH:33]([CH:37]([CH3:39])[CH3:38])[C:34](O)=[O:35])=[O:31])([CH3:28])([CH3:27])[CH3:26]>>[C:22]([C:12]1[CH:13]=[N:14][C:15]2[C:20]([C:11]=1[NH:10][C@H:7]1[CH2:8][CH2:9][C@H:4]([NH:3][C:34](=[O:35])[CH:33]([NH:32][C:30](=[O:31])[O:29][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:37]([CH3:39])[CH3:38])[CH2:5][CH2:6]1)=[N:19][C:18]([Cl:21])=[CH:17][CH:16]=2)(=[O:24])[CH3:23]

Participants

3

Reactant 2

HCID 270655Boc-DL-valineHCID 117774125HCID 117774125, compound

Product 1

HCID 178467149HCID 178467149, compoundYield 65.7%

Procedure

Following general procedure VI, 1-{4-[(4-aminocyclohexyl)amino]-6-chloro-1,5-naphthyridin-3-yl}ethanone dihydrochloride (300 mg, 0.94 mmol) was reacted with 2-[(tert-butoxycarbonyl)amino]-3-methylbutanoic acid (310 mg, 1.4 mmol) to afford the desired product (320 mg, 65%) as a white solid. ESI MS m/z 518 [M+H]+

Sources & evidence

ORD record
ord-8461c6a4ee464153917d575fb26f43a9
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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