Diisopropylethylamine → [(2R)-2-(Cyclopentylmethyl)-3-(2-{5-fluoro-2-(fluoromethyl)-6-[(9aS)-hexahydropyrazino[2,1-c][1,4]oxazin-8(1H)-yl]-4-pyrimidinyl}hydrazino)-3-oxopropyl]hydroxyformamide

HRID 1366649Notes

Reaction equation

HRID 1366649 reaction equation
[CH:1]1([CH2:6][C@@H:7]([C:13]([NH:15][NH:16][C:17]2[C:22]([F:23])=[C:21]([N:24]3[CH2:28][CH2:27][C@@H:26]([CH2:29][OH:30])[CH2:25]3)[N:20]=[C:19]([CH3:31])[N:18]=2)=[O:14])[CH2:8][N:9]([OH:12])[CH:10]=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C([F:39])=C(Cl)N=C(CF)N=1.[CH3:43][CH2:44][N:45](C(C)C)C(C)C>>[CH:1]1([CH2:6][C@@H:7]([C:13]([NH:15][NH:16][C:17]2[C:22]([F:23])=[C:21]([N:24]3[CH2:28][CH2:27][N:45]4[C@H:26]([CH2:29][O:30][CH2:43][CH2:44]4)[CH2:25]3)[N:20]=[C:19]([CH2:31][F:39])[N:18]=2)=[O:14])[CH2:8][N:9]([OH:12])[CH:10]=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 58000547HCID 58000547, compoundHCID 58000764HCID 58000764, compound

Product 1

HCID 58000743[(2R)-2-(Cyclopentylmethyl)-3-(2-{5-fluoro-2-(fluoromethyl)-6-[(9aS)-hexahydropyrazino[2,1-c][1,4]oxazin-8(1H)-yl]-4-pyrimidinyl}hydrazino)-3-oxopropyl]hydroxyformamide

Procedure

[(2R)-2-(Cyclopentylmethyl)-3-(2-{5-fluoro-2-(fluoromethyl)-6-[(9aS)-hexahydropyrazino[2,1-c][1,4]oxazin-8(1H)-yl]-4-pyrimidinyl}hydrazino)-3-oxopropyl]hydroxyformamide was prepared according to General Procedure A, utilizing (9aS)-octahydropyrazino[2,1-c][1,4]oxazine dihydrochloride (Example 22) in place of pyrrolidine, using 4,6-dichloro-5-fluoro-2-(fluoromethyl)pyrimidine in place of 4,6-dichloro-5-fluoro-2-methylpyrimidine, and using 3 equivalents of DIPEA in Part A. LCMS: (M+H)+: 498.3.

Sources & evidence

ORD record
ord-1490c7afc2ec4e28b2be8223b17a4569
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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