5-Fluoro-1,2,3,4-tetrahydroisoquinoline--hydrogen chloride (1/1) → HCID 90410954, compound

HRID 717398Notes

Reaction equation

HRID 717398 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]=[C:16]([C:18]([OH:20])=O)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.Cl.[F:22][C:23]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:24]=1[CH2:25][CH2:26][NH:27][CH2:28]2>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]=[C:16]([C:18]([N:27]3[CH2:26][CH2:25][C:24]4[C:29](=[CH:30][CH:31]=[CH:32][C:23]=4[F:22])[CH2:28]3)=[O:20])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 450740065-Fluoro-1,2,3,4-tetrahydroisoquinoline--hydrogen chloride (1/1)HCID 904114972-(4-Fluorophenyl)quinazoline-4-carboxylic acid

Product 1

HCID 90410954HCID 90410954, compoundYield 27%

Procedure

Reaction of 2-(4-fluorophenyl)quinazoline-4-carboxylic acid with 5-fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 10 (27.0% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 2.88 and 3.13 (2t, 2H), 3.64 and 4.24 (2t, 2H), 4.58 and 5.14 (2s, 2H), 6.68-7.33 (m, 5H), 7.65-7.77 (m, 1H), 7.94-8.10 (m, 2H), 8.15-8.20 (m, 1H), 8.57-8.67 (m, 2H); 19F (282 MHz, DMSO-d6) δ −112.0, −121.0; MS (ESI) m/z 402 ([M+H]+).

Sources & evidence

ORD record
ord-682fb81c5f404e5b8f588f5baa77f4f0
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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