HCID 15292728, compound → HCID 19379107, compound

HRID 2210606Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[N:11]3[CH:12]=[CH:13][C:14]([C:15]([C:17]4[C:25]5[C:20](=[CH:21][C:22]([C:26]6[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=6)=[CH:23][CH:24]=5)[N:19]([CH2:33][CH2:34][NH:35]C(OC(C)(C)C)=O)[CH:18]=4)=[O:16])=[C:10]3[CH2:9][S:8]2)[CH:2]=1.[ClH:43].O1CCOCC1>C(Cl)Cl>[ClH:43].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[N:11]3[CH:12]=[CH:13][C:14]([C:15]([C:17]4[C:25]5[C:20](=[CH:21][C:22]([C:26]6[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=6)=[CH:23][CH:24]=5)[N:19]([CH2:33][CH2:34][NH2:35])[CH:18]=4)=[O:16])=[C:10]3[CH2:9][S:8]2)[CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3-(pyridin-3-yl)-7-[1-(2-tert-butoxycarbonylaminoethyl)-6-(4-fluorophenyl)indol-3-ylcarbonyl]-1H,3H-pyrrolo[1,2-c]thiazole (104 mg), prepared as in Example 57, in CH2Cl2 at 0° C. was treated with 4N HCl/dioxane (1 mL). The reaction mixture was stirred for 15 min at 0° C. and then concentrated in vacuo. The resulting solid was azeotroped three times with CH2Cl2 to give 3-(Pyridin-3-yl)-7-[1-(2-aminoethyl)-6-(4-fluorophenyl)indol-3-ylcarbonyl]-1H,3H-pyrrolo[1,2-c]thiazole hydrochloride (115 mg), 1H NMR (D3COD, 300 MHz) δ3.48-3.60 (m, 3H), 3.64-3.75 (m, 4H), 4.53 (d, 1H, J=15 Hz) 4.68-4.77 (m, 3H), 6.76 (d, 1H, J=3 Hz), 6.9 (d, 1H, J=1.5 Hz), 7.55 (dd, 1H, J=1.5 9 Hz), 7.75 (dd, 2H, J=6, 8 Hz), 7.83 (s, 1H), 8.13 (dd, 1H, J=6, 8 Hz), 8.30 (s, 1H), 8.35 (d, 1H, J=9 Hz), 8.49 (d, 1H, J=9 Hz), 8.87 (d, 2H, J=7 Hz), MS (DCI/NH3) m/e 483 (M+H)+.

Workup

concentrationconcentrated in vacuo
customThe resulting solid was azeotroped three times with CH2Cl2

Sources & evidence

ORD record: ord-2365e7211dc44c0c9848a9b1a8137d02
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05459152

Reaction notes

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