Diisopropylethylamine → HCID 24936373, compound

HRID 2424832Notes

Reaction equation

HRID 2424832 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.Cl[C:8]1[CH:17]=[CH:16][C:15]2[C:14]([C:18]([NH:20][CH2:21][C@:22]3([OH:29])[CH2:27][CH2:26][CH2:25][C@H:24]([CH3:28])[CH2:23]3)=[O:19])=[C:13]([Cl:30])[CH:12]=[CH:11][C:10]=2[N:9]=1.C(N(C(C)C)CC)(C)C>C(#N)C>[Cl:30][C:13]1[CH:12]=[CH:11][C:10]2[N:9]=[C:8]([N:4]3[CH2:5][CH2:6][C@H:2]([OH:1])[CH2:3]3)[CH:17]=[CH:16][C:15]=2[C:14]=1[C:18]([NH:20][CH2:21][C@:22]1([OH:29])[CH2:27][CH2:26][CH2:25][C@H:24]([CH3:28])[CH2:23]1)=[O:19]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2733874(3S)-pyrrolidin-3-olHCID 866233642,6-Dichloro-N-{[(1S,3S)-1-hydroxy-3-methylcyclohexyl]methyl}quinoline-5-carboxamide

Product 1

HCID 24936373HCID 24936373, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

(S)-3-hydroxypyrrolidine (80 mg) was added to a suspension of the product of step d) (0.2 g) and diisopropylethylamine (300 μl) in acetonitrile (3 ml). The reaction mixture was heated in a microwave (100 W) for 30 minutes at 120° C. before being concentrated in vacuo. Water (15 ml) was added and the suspension sonicated for 10 minutes. The solid was filtered and dried in vacuo overnight to afford the title compound as a cream solid (180 mg). m.p. 222° C. (acetonitrile).

Workup

  1. concentrationbefore being concentrated in vacuo
  2. additionWater (15 ml) was added
  3. customthe suspension sonicated for 10 minutes
  4. filtrationThe solid was filtered
  5. customdried in vacuo overnight

Sources & evidence

ORD record
ord-9f6f1da8fc344f20bb2380ffd33816ab
Source dataset
uspto-grants-2011_06
Patent number
US07964616B2

Reaction notes

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