D-Alpha-aminobutyric acid → 2-Chloro-5-methyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

HRID 44809

반응식

HRID 44809 반응식
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[C:7]([OH:9])=O.N[C@H](CC)C(O)=O.N[C@H](CC)C(OC)=O.CO[C:27]([CH:29]1[CH2:34]OC[CH2:31][NH:30]1)=O.[Cl:35][C:36]1[N:41]=C(Cl)C([N+]([O-])=O)=C[N:37]=1.ClC1N=C(N(C2CCCC2)[C@H](CC)C(OC)=O)C([N+]([O-])=O)=CN=1>>[Cl:35][C:36]1[N:41]=[CH:34][C:29]2[N:30]([CH3:31])[C:7](=[O:9])[CH:2]3[CH2:3][O:4][CH2:5][CH2:6][N:1]3[C:27]=2[N:37]=1

참가 물질

7

반응물 6

HCID 439691D-Alpha-aminobutyric acidHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 3286806Methyl 3-MorpholinecarboxylateHCID 33401523-Morpholinecarboxylic acidHCID 13283514methyl (2R)-2-aminobutanoateHCID 58405447(R)-Methyl 2-((2-chloro-5-nitropyrimidin-4-yl)(cyclopentyl)amino)butanoate

생성물 1

HCID 584052812-Chloro-5-methyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

실험 절차

Intermediate I was prepared in the same manner as Intermediate B, using 3-morpholinecarboxylic acid as the starting material instead of (R)-2-aminobutanoic acid. No reductive amination step, such as that used for the conversion of compound II to compound III, was required. Rather, methylmorpholine-3-carboxylate was reacted directly with 2,4-dichloro-5-nitropyrimidine in the same manner as is described for the conversion of compound III to Intermediate A. LCMS: 254.9 m/z (M+H)+.

출처 및 근거

ORD 기록
ord-7a344267664e4517b6f16e4125cc4cfa
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541418B2

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