Water → HCID 53251495, compound

HRID 2092162Notes

Reaction equation

N[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[Cl:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[CH3:23])[O:19][CH2:18][CH2:17][CH:16]2[NH2:24].FC(F)(F)C1C=C2C([CH:31]([NH2:37])CCO2)=CC=1.[OH2:40]>>[Cl:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[CH3:23])[O:19][CH2:18][CH2:17][CH:16]2[NH:24][C:31]([NH:37][C:9]1[CH:10]=[CH:11][CH:2]=[C:7]2[C:8]=1[CH:3]=[CH:4][CH:5]=[N:6]2)=[O:40]

Participants

Reactant 4

HCID 962Water

HCID 707665-Aminoisoquinoline

HCID 166430296-Chloro-7-methyl-3,4-dihydro-2H-1-benzopyran-4-amine

HCID 468354217-(Trifluoromethyl)chroman-4-amine

Product 1

HCID 53251495HCID 53251495, compound

Procedure

The title compound was prepared using the procedure as described in Example 5, substituting 5-aminoquinoline for 5-aminoisoquinoline and substituting the product of Example 13B for the product of Example 4D. 1H NMR (300 MHz, DMSO-d6) δ 8.90 (m, 1H), 8.62 (s, 1H), 8.47 (m, 1H), 8.12 (m, 1H), 7.70 (m, 2H), 7.58 (m, 1H), 7.31 (s, 1H), 7.07 (d, J=7.5 Hz, 1H), 7.18-7.00 (m, 3H), 6.82 (s, 1H), 4.91 (m, 1H), 4.33-4.10 (m, 2H), 2.24 (s, 3H), 2.20-1.92 (m, 2H). MS (ESI) m/e 368 (M−H)+. Calcd. For C20H18N3O2Cl.0.2; H2O: C, 64.67; H, 4.99; N, 11.31. Found: C, 64.85; H, 4.90; N, 11.02.

Sources & evidence

ORD record: ord-213a1244910b4b43847481e84c42f658
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440691B2

Reaction notes

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