Diisopropylethylamine → (5-Chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidin-2-yl)-[4-(1-hydroxy-1-methylethyl)piperidin-1-yl]methanone

HRID 1922766ノート

反応式

HRID 1922766 の反応式
[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[N:10]=[C:9]([C:11]([OH:13])=O)[S:8][C:6]=2[N:7]=1.[NH:20]1[CH2:25][CH2:24][CH:23]([C:26]([OH:29])([CH3:28])[CH3:27])[CH2:22][CH2:21]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[N:10]=[C:9]([C:11]([N:20]3[CH2:25][CH2:24][CH:23]([C:26]([OH:29])([CH3:28])[CH3:27])[CH2:22][CH2:21]3)=[O:13])[S:8][C:6]=2[N:7]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 52003212-(4-Piperidyl)-2-propanolHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866482365-Chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine-2-carboxylic acid

生成物 1

HCID 59605242(5-Chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidin-2-yl)-[4-(1-hydroxy-1-methylethyl)piperidin-1-yl]methanone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 5-chloro-7-morpholin-4-ylthiazolo[5,4-d]pyrimidine-2-carboxylic acid (200 mg, 0.67 mmol), 2-piperidin-4-ylpropan-2-ol (105 mg, 0.73 mmol), HATU (278 mg, 0.73 mmol) and DIPEA (130 μL, 0.75 mmol) in DCM (7 mL) was allowed to stir at r.t. for 18 h. The reaction mixture was concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, MeOH:DCM, 0-2%) affording the title compound as a white solid. 1H NMR (CDCl3, 400 MHz): δ 5.15 (1 H, d, J=13.36 Hz), 4.79 (1 H, d, J=13.25 Hz), 4.35 (4 H, brd s), 3.85 (4 H, t, J=4.75 Hz), 3.16-3.13 (1 H, m), 1.92 (2 H, t, J=15.39 Hz), 1.75-1.60 (1 H, m), 1.49-1.38 (4 H, m), 1.22 (6 H, d, J=6.97 Hz).

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting residue purified by column chromatography (Si—PCC, MeOH:DCM, 0-2%)

出典と根拠

ORDレコード
ord-6e64d7503c5e4990b6132fd4b7000a2d
出典データセット
uspto-grants-2012_05
特許番号
US08173650B2

反応ノート

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