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Methylamine → 2-{7-Chloro-4-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}-N-methylacetamide

HRID 1054189
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인쇄 미리보기

반응식

HRID 1054189 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]([C:11]([C:13]3[CH:23]=[CH:22][C:16]4[O:17][CH2:18][C:19](=[O:21])[NH:20][C:15]=4[CH:14]=3)=[O:12])[CH:9]([CH2:24][C:25]([OH:27])=O)[CH2:8][O:7][C:6]=2[CH:28]=1.[CH3:29][NH2:30].C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]([C:11]([C:13]3[CH:23]=[CH:22][C:16]4[O:17][CH2:18][C:19](=[O:21])[NH:20][C:15]=4[CH:14]=3)=[O:12])[CH:9]([CH2:24][C:25]([NH:30][CH3:29])=[O:27])[CH2:8][O:7][C:6]=2[CH:28]=1
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참가 물질

5

반응물 3

HCID 6329MethylamineHCID 111923Propylphosphonic anhydrideHCID 1185996432-(7-chloro-4-(3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-3-yl)acetic acid2회

생성물 1

HCID 1185996182-{7-Chloro-4-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}-N-methylacetamide수율 64.1%

시약·촉매·용매 1

HCID 8857
Ethyl Acetate
용매

실험 절차

A mixture of 2-(7-chloro-4-(3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-3-yl)acetic acid (Intermediate 22, 38 mg, 0.09 mmol), methanamine (0.236 mL, 0.47 mmol) (2 M solution in THF), and TEA (0.039 mL, 0.28 mmol) in EtOAc (2 mL) was treated with T3P (50 wt. % in EtOAc, 0.112 mL, 0.19 mmol) at rt. The reaction mixture was stirred at rt over night and concentrated. The crude product was purified by preparative HPLC (Kromasil C8 column (10 μm 250×20 ID mm), using a gradient of 20-60% ACN in H2O/ACN/FA 95/5/0.2 buffer, over 20 min with a flow of 19 mL/min, UV detection at 240 nm). Freeze-drying gave the title compound (24 mg, 61%) as a white powder.

후처리

  1. concentrationconcentrated
  2. customThe crude product was purified by preparative HPLC (Kromasil C8 column (10 μm 250×20 ID mm)
  3. customFreeze-drying

출처 및 근거

ORD 기록
ord-a4c091a3cb8e4794ad4caed3765d5ad0
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09394291B2

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