4-Morpholinecarbonyl chloride → 1-(Morpholine-4-carbonyl)indoline-5-sulfonamide

HRID 528840Notes

Reaction equation

HRID 528840 reaction equation
C1([C:7]([N:9]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:15][CH:16]=3)[CH2:11][CH2:10]2)=[O:8])CCCCC1.N1C2C(=CC(S(N)(=O)=O)=CC=2)CC1.[N:35]1(C(Cl)=O)[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>>[N:35]1([C:7]([N:9]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([NH2:21])(=[O:19])=[O:20])=[CH:15][CH:16]=3)[CH2:11][CH2:10]2)=[O:8])[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1

Participants

4

Reactant 3

HCID 848104-Morpholinecarbonyl chlorideHCID 80272522,3-dihydro-1H-indole-5-sulfonamide2×HCID 606987421-(Cyclohexanecarbonyl)indoline-5-sulfonamide

Product 1

HCID 710610131-(Morpholine-4-carbonyl)indoline-5-sulfonamideYield 59%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 55, indoline-5-sulfonamide (Intermediate 54A, 250 mg, 1.26 mmol) and morpholine-4-carbonyl chloride (206 μL, 1.77 mmol) were converted to the title compound (230 mg, 59%) after purification using preparative HPLC. 1H NMR (DMSO-d6) δ 7.61-7.58 (m, 2H), 7.15-7.12 (m, 3H), 3.92 (t, J=6.5 Hz, 2H), 3.78-3.75 (m, 2H), 3.66-3.63 (m, 4H), 3.10-3.07 (m, 4H); MS(ESI+) m/z 312.2 (M+H)+.

Sources & evidence

ORD record
ord-34e0548f4ac84328ae2e84823bb191f5
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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