Diisopropylethylamine → HCID 59023866, compound

HRID 1678224Notes

Reaction equation

HRID 1678224 reaction equation
[S:1]1[C:5]([C:6]2[CH:7]=[C:8]([NH2:15])[CH:9]=[C:10]3[C:14]=2[NH:13][N:12]=[CH:11]3)=[CH:4][C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]1=2.C(N(C(C)C)C(C)C)C.[O:29]=[C:30]1[NH:35][C:34]2[CH:36]=[C:37]([S:40](Cl)(=[O:42])=[O:41])[CH:38]=[CH:39][C:33]=2[O:32][CH2:31]1>CN(C=O)C>[S:1]1[C:5]([C:6]2[CH:7]=[C:8]([NH:15][S:40]([C:37]3[CH:38]=[CH:39][C:33]4[O:32][CH2:31][C:30](=[O:29])[NH:35][C:34]=4[CH:36]=3)(=[O:42])=[O:41])[CH:9]=[C:10]3[C:14]=2[NH:13][N:12]=[CH:11]3)=[CH:4][C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]1=2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 52002293-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-sulfonyl chlorideHCID 59023728HCID 59023728, compound

Product 1

HCID 59023866HCID 59023866, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 7-benzo[b]thiophen-2-yl-1H-indazol-5-ylamine (Example #F.8.1, 32 mg, 0.12) and ethyl-diisopropylamine (0.032 mL, 0.18 mmol) in DMF (1 mL) at room temperature and under an inert atmosphere was added 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-sulfonyl chloride (33 mg, 0.13 mmol). The reaction mixture was stirred at room temperature for 2 hours then concentrated under reduced pressure. The crude material was purified by preparative HPLC (20% to 80% acetonitrile/0.05 M aqueous ammonium acetate, buffered to pH 4.5 over 30 min at 20 mL/min; Hyperprep C18, 300 Å, 8 μm, 250×21.1 mm column) to afford 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-sulfonic acid (7-benzo[b]thiophen-2-yl-1H-indazol-5-yl)-amide as a white solid (34 mg, 58%). LC/MS (Table 1, Method e) Rt 1.75 min; ESI−MS [M+H]+=475.3.

Workup

  1. customat room temperature
  2. concentrationthen concentrated under reduced pressure
  3. customThe crude material was purified by preparative HPLC (20% to 80% acetonitrile/0.05 M aqueous ammonium acetate, buffered to pH 4.5 over 30 min at 20 mL/min; Hyperprep C18, 300 Å, 8 μm, 250×21.1 mm column)

Sources & evidence

ORD record
ord-e1c14b43b1424ead8331a2f1a66a3899
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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