Hydrochloric Acid → HCID 66715803, compound

HRID 2271889Notes

Reaction equation

HRID 2271889 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([NH:13][C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([C:24]5[CH:29]=[C:28]([F:30])[C:27]([OH:31])=[C:26]([Cl:32])[CH:25]=5)[CH:22]=4)[N:17]=[CH:16][C:15]=3[C:33]([CH:35]3[CH2:37][CH2:36]3)=[O:34])=[CH:9][N:8]=2)[CH2:3]1.Cl>CO.C(OCC)C>[ClH:32].[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[N:8]=[CH:9][C:10]([NH:13][C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([C:24]5[CH:29]=[C:28]([F:30])[C:27]([OH:31])=[C:26]([Cl:32])[CH:25]=5)[CH:22]=4)[N:17]=[CH:16][C:15]=3[C:33]([CH:35]3[CH2:36][CH2:37]3)=[O:34])=[CH:11][N:12]=2)[CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66715296HCID 66715296, compound

Product 1

HCID 66715803HCID 66715803, compoundYield 198%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

(4-(2-(3-aminopyrrolidin-1-yl)pyrimidin-5-ylamino)-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-3-yl)(cyclopropyl)methanone (30 mg, 0.06 mmol) was suspended in methanol (1 mL) at 0° C. followed by dropwise addition of HCl in diethyl ether (2 M) until complete dissolution of the solid was observed. The solvent was removed under reduced pressure to afford the desired product (33 mg, 92%) as a yellow-orange solid: 1H NMR (500 MHz, MeOD) δ 9.31 (br s, 1H), 8.45 (s, 2H), 8.23-8.14 (m, 2H), 8.02 (d, J=8.8 Hz, 1H), 7.26-7.20 (m, 2H), 4.11-4.00 (m, 2H), 3.94-3.73 (m, 3H), 2.83 (br s, 1H), 2.58-2.48 (m, 1H), 2.28-2.17 (m, 1H), 1.22-1.14 (m, 4H), 0.92-0.88 (s, 0H). ESI MS m/z 519 [C27H24ClFN6O2+H]+; HPLC>99.0% (AUC), tR=5.18 min.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9576defae31b4efcaafb6fec89281122
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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