D-Lactic Acid → (R)-2-hydroxy-1-(4-(3-(6-phenylpyridin-3-yl)-8H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidin-5-yloxy)piperidin-1-yl)propan-1-one

HRID 1913259노트

반응식

HRID 1913259 반응식
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[CH:14]=[N:15][N:16]4[C:21]5[NH:22][CH:23]=[CH:24][C:20]=5[C:19]([O:25][CH:26]5[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]5)=[N:18][C:17]=34)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:32](O)(=[O:36])[C@@H:33]([CH3:35])[OH:34].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[OH:34][C@H:33]([CH3:35])[C:32]([N:29]1[CH2:30][CH2:31][CH:26]([O:25][C:19]2[C:20]3[CH:24]=[CH:23][NH:22][C:21]=3[N:16]3[N:15]=[CH:14][C:13]([C:10]4[CH:11]=[N:12][C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)=[CH:8][CH:9]=4)=[C:17]3[N:18]=2)[CH2:27][CH2:28]1)=[O:36]

참가 물질

7

반응물 4

HCID 61503D-Lactic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1363324193-(6-phenylpyridin-3-yl)-5-(piperidin-4-yloxy)-8H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidine

생성물 1

HCID 135998754(R)-2-hydroxy-1-(4-(3-(6-phenylpyridin-3-yl)-8H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidin-5-yloxy)piperidin-1-yl)propan-1-one

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 3-(6-phenylpyridin-3-yl)-5-(piperidin-4-yloxy)-8H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidine (Int-11e, 95.8 mg, 0.23 mmoL), D-(−)-lactic acid (25 mg, 0.28 mmoL), EDC (89 mg, 0.47 mmoL), HOBt (63 mg, 0.47 mmoL) and DIEA (244 uL, 1.46 mmoL) in DMF (4 mL) were stirred at room temperature for 2 hr. Purification with prep-LC provided (R)-2-hydroxy-1-(4-(3-(6-phenylpyridin-3-yl)-8H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidin-5-yloxy)piperidin-1-yl)propan-1-one (35): LCMS tR=3.48 Min (10 min run, UV254nm). Mass calculated for, M+482.2, observed m/z 483.2 (M+H).

후처리

  1. customPurification

출처 및 근거

ORD 기록
ord-5cdd4753711045259540a738d8032c79
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609675B2

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