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 1913259ノート

反応式

HRID 1913259 の反応式
[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]

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  1. customPurification

出典と根拠

ORDレコード
ord-5cdd4753711045259540a738d8032c79
出典データセット
uspto-grants-2013_12
特許番号
US08609675B2

反応ノート

読み込み中…