Hydrochloric Acid → HCID 78323680, compound

HRID 2170154Notes

Reaction equation

C([NH:5][S:6]([C:9]1[CH:10]=[N:11][CH:12]=[C:13]([C:15]2[N:20]=[C:19]([NH:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[C:18]3=[C:29]([C:32]4[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=4)[CH:30]=[CH:31][N:17]3[N:16]=2)[CH:14]=1)(=[O:8])=[O:7])(C)(C)C.Cl>O1CCOCC1>[F:38][C:35]1[CH:34]=[CH:33][C:32]([C:29]2[CH:30]=[CH:31][N:17]3[C:18]=2[C:19]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[N:20][C:15]([C:13]2[CH:14]=[C:9]([S:6]([NH2:5])(=[O:8])=[O:7])[CH:10]=[N:11][CH:12]=2)=[N:16]3)=[CH:37][CH:36]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of N-(tert-butyl)-5-(5-(4-fluorophenyl)-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide (30.0 mg, 0.0560 mmol) in dioxane (5 mL) was added 2 mL of 5 N HCl in dioxane. The contents were heated at 50° C. for 12 h. The solvents were removed under reduced pressure to give a white solid. The solid was purified by preparative HPLC (Condition B-61 as described in general methods) to give 5-(5-(4-fluorophenyl)-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide (19.0 mg, 44.0%) as an off-white solid. LCMS Condition B-23: retention time 1.91 min, [M+1]=476.2. HPLC Condition B-1: retention time 8.03 min, Purity=98.30%. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.93 (d, J=4.8 Hz, 2H), 6.84 (d, J=2.8 Hz, 1H), 7.25-7.52 (m, 5H), 7.52-7.62 (m, 4H) 7.79 (t, J=1.6 Hz, 1H), 7.88 (d, J=2.8 Hz, 1H), 8.35 (s, 1H), 8.92 (s, 1H), 9.05 (s, 1H), 9.65 (s, 1H).

Workup

customThe solvents were removed under reduced pressure
customto give a white solid
customThe solid was purified by preparative HPLC (Condition B-61 as described in general methods)

Sources & evidence

ORD record: ord-f03b83ebcb8c4ba8befe1904857f50ed
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09050345B2

Reaction notes

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