Diisopropylethylamine → HCID 118566617, compound

HRID 1056732Notes

Reaction equation

HRID 1056732 reaction equation
[OH:1][C@@:2]1([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[CH:16][C:17](Cl)=[N:18][C:19]=3[CH:20]=[CH:21][C:22]=2[Cl:23])=[O:12])[CH2:7][CH2:6][CH2:5][C@H:4]([CH3:8])[CH2:3]1.ClC1C=C[C:33]2[C:32]([C:36]([OH:38])=O)=[C:31](Cl)C=C[C:28]=2[N:27]=1.CCN(C(C)C)C(C)C.OCC1CCNC1>>[OH:1][C@@:2]1([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[CH:16][C:17]([N:27]4[CH2:28][CH2:33][CH:32]([CH2:36][OH:38])[CH2:31]4)=[N:18][C:19]=3[CH:20]=[CH:21][C:22]=2[Cl:23])=[O:12])[CH2:7][CH2:6][CH2:5][C@H:4]([CH3:8])[CH2:3]1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 13400657(Pyrrolidin-3-yl)methanolHCID 131736436HCID 131736436, compound

Product 1

HCID 118566617HCID 118566617, compound

Procedure

The title compound was synthesized according to the procedure described in example 1 using 2,6-dichloro-quinoline-5-carboxylic acid 2,6-Dichloro-quinoline-5-carboxylic acid ((1S,3S)-1-hydroxy-3-methyl-cyclohexylmethyl)-amide, DIPEA and 3-(1-hydroxy-methyl)-pyrrolidine. 1H NMR (400 MHz, DMSO-d6): δ 8.49 (t, J=6.16 Hz, 1H), 7.80 (d, J=9.28 Hz, 1H), 7.53-7.47 (m, 2H), 6.94 (d, J=9.32 Hz, 1H), 4.73-4.72 (m, 1H), 4.15 (s, 1H), 3.64-3.49 (m, 2H), 3.47-3.41 (m, 3H), 2.42 (s, 1H), 2.05-2.03 (m, 1H), 1.79-1.60 (m, 2H), 1.60-1.47 (m, 5H), 1.29-1.28 (m, 1H), 1.18-1.17 (m, 1H), 0.84-0.82 (m, 3H), 0.75-0.75 (m, 1H) m/z: 432.2 [M+H]+

Sources & evidence

ORD record
ord-05e4c24b0e27450abacf2895bc59645b
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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