1-(Benzenesulfonyl)-1H-indol-5-amine → Acetic Acid 3-[4-(1-benzenesulfonyl-1H-indol-5-ylamino)-quinazolin-6-yl]-allyl ester

HRID 1264057Notes

Reaction equation

O([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:18]=[CH:19][CH2:20][O:21][C:22](=[O:24])[CH3:23])[CH:16]=2)[N:11]=[CH:10][N:9]=1)C1C=CC=CC=1.[NH2:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[N:31]([S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:37])=[O:36])[CH:30]=[CH:29]2>C1(O)C=CC=CC=1>[C:38]1([S:35]([N:31]2[C:32]3[C:28](=[CH:27][C:26]([NH:25][C:8]4[C:17]5[C:12](=[CH:13][CH:14]=[C:15]([CH:18]=[CH:19][CH2:20][O:21][C:22](=[O:24])[CH3:23])[CH:16]=5)[N:11]=[CH:10][N:9]=4)=[CH:34][CH:33]=3)[CH:29]=[CH:30]2)(=[O:36])=[O:37])[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of ester 26 (630 mg, 1.97 mmol) and 5-amino-1-phenylsulfonylindole in phenol (3.0 g) was heated at 100° C. for 20 hours. Excess phenol was removed by distillation and the resulting brown oil was purified by silica gel chromatography eluting with 1:1 ethyl acetate:hexanes then ethyl acetate. Quinazoline 27 (430 mg, 43%) was obtained as an off-white waxy solid. 1H NMR (CDCl3; 400 MHz): δ: 8.61 (s, 1H), 7.92 (m, 3H), 7.82 (m, 4H), 7.51 (m, 2H), 7.43 (m, 3H), 6.74 (d, 1H), 6.62 (d, 1H), 6.45 (dt, 1H), 4.74 (dd, 2H), 2.09 (s, 3H).

Workup

customExcess phenol was removed by distillation
customthe resulting brown oil was purified by silica gel chromatography
washeluting with 1:1 ethyl acetate

Sources & evidence

ORD record: ord-4a236376a3d4400e86e075b7f4696192
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06541481B2

Reaction notes

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