Aminoacetaldehyde dimethyl acetal → HCID 66631436, compound

HRID 931801Notes

Reaction equation

HRID 931801 reaction equation
C([O:7][CH2:8][C@@H:9]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[C:10]1[C:11]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15](OS(C(F)(F)F)(=O)=O)[CH:14]=[CH:13]2)(=O)C(C)(C)C.CO[CH:43](OC)[CH2:44][NH2:45].C[O:49]C(OC)[C@@H](N)C(C)C>>[C:37]([O:36][C@@H:9]([C:10]1[C:11]([C:29]2[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]1[CH:43]=[CH:44][N:45]=[C:15]1[CH:14]=[CH:13]2)[C:8]([OH:49])=[O:7])([CH3:40])([CH3:38])[CH3:39]

Participants

4

Reactant 3

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 552899682-Butanamine, 1,1-dimethoxy-3-methyl-, (S)-HCID 86691982(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(trifluoromethylsulfonyloxy)quinolin-6-yl)ethyl pivalate

Product 1

HCID 66631436HCID 66631436, compound

Procedure

(S)-2-tert-Butoxy-2-(6-(4-chlorophenyl)-8-methylimidazo[1,2-a]quinolin-7-yl)acetic acid (62) was prepared in a similar manner as compound (S)-2-tert-butoxy-2-((R)-6-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)-2-isopropyl-8-methylimidazo[1,2-a]quinolin-7-yl)acetic acid of Example 60 except using (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(trifluoromethylsulfonyloxy)quinolin-6-yl)ethyl pivalate and 2,2-dimethoxyethanamine instead of (S)-2-tert-butoxy-2-((R)-5-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)-7-methyl-2-(trifluoromethylsulfonyloxy)quinolin-6-yl)ethyl pivalate and (S)-1,1-dimethoxy-3-methylbutan-2-amine. 1H-NMR 400 MHz (CD3OD) δ 8.92 (m, 1 H), 8.45 (m, 1 H), 8.10 (m, 1 H), 7.7-7.6 (m, 5 H), 7.38 (m, 1 H), 5.21 (s, 1 H), 2.80 (s, 3 H), 0.99 (s, 9 H); LCMS-ESI+ (m/z): [M+H]+ calcd for C24H24ClN2O3: 423. Found: 423.2; LCMS-ESI+ (m/z): [M+H]+ calcd for C24H22ClN2O3: 421.1. Found: 421.0.

Sources & evidence

ORD record
ord-39add201ca9249d2b40acb581ee15f7d
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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