1,2-Dichloroethane → HCID 86632319、化合物

HRID 1695945

反応式

HRID 1695945 の反応式
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH:9][C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[CH:17]2[N:21]([CH2:22][CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:20](=[O:28])[CH:19]([CH2:29][C:30]([OH:32])=O)[S:18]2)[CH2:3][CH2:2]1.[NH:33]1[CH2:38][CH2:37][CH:36]([N:39]2[CH2:45][CH2:44][C:43]3[CH:46]=[CH:47][CH:48]=[CH:49][C:42]=3[NH:41][C:40]2=[O:50])[CH2:35][CH2:34]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O>[O:1]1[CH2:2][CH2:3][N:4]([CH2:7][CH2:8][NH:9][C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[CH:17]2[N:21]([CH2:22][CH2:23][C:24]([CH3:25])([CH3:27])[CH3:26])[C:20](=[O:28])[C@H:19]([CH2:29][C:30]([N:33]3[CH2:34][CH2:35][CH:36]([N:39]4[CH2:45][CH2:44][C:43]5[CH:46]=[CH:47][CH:48]=[CH:49][C:42]=5[NH:41][C:40]4=[O:50])[CH2:37][CH2:38]3)=[O:32])[S:18]2)[CH2:5][CH2:6]1

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 113795873-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 866323182-(2-(2-(2-Morpholinoethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid

生成物 1

HCID 86632319HCID 86632319、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2-(2-(2-(2-Morpholinoethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid (420.8 mg, 0.9 mmol), 3-(piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one (441 mg, 1.798 mmol), EDC (354 mg, 1.847 mmol), and HOBt (273 mg, 1.783 mmol) were stirred in DMF (5 mL) at RT. The mixture was transferred to a separatory funnel, then diluted with 100 mL EtOAc and washed with a saturated sodium bicarbonate solution. The aqueous layer was extracted 3× with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated. The crude material was purified by reverse phase chromatography to give 3-(1-(2-((5S)-2-(2-(2-morpholinoethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetyl)piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one. LC/MS: 695.33 (M+1) Rt=2.20 min (10-90% 3/5 min (grad/run) w/formic acid.

後処理

  1. customThe mixture was transferred to a separatory funnel
  2. washwashed with a saturated sodium bicarbonate solution
  3. extractionThe aqueous layer was extracted 3× with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude material was purified by reverse phase chromatography

出典と根拠

ORDレコード
ord-7ca44e2460b7452b82cd3855b8d1e9e3
出典データセット
uspto-grants-2012_04
特許番号
US08163737B2

関連ノート

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