1,2-Dichloroethane → HCID 86710215, compound
Reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=O.C1C=CC2N(O)N=NC=2C=1.C(Cl)C[Cl:31].[CH3:33][C:34]1[C:42]2[C:37]([NH:38][CH:39]=[N:40][C:41]=2[N:43]2[CH2:48][CH2:47][CH:46]([NH2:49])[CH2:45][CH2:44]2)=[N:36][CH:35]=1.CCN(C(C)C)C(C)C>ClCCl.CN1CCCC1=O>[ClH:31].[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([NH:49][CH:46]1[CH2:45][CH2:44][N:43]([C:41]2[C:42]3[C:34]([CH3:33])=[CH:35][NH:36][C:37]=3[N:38]=[CH:39][N:40]=2)[CH2:48][CH2:47]1)=[O:15]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 3-({2-[(2R)-2-methyl-1-pyrrolidinyl]ethyl}oxy)benzoic acid D54 (116 mg), HOBT (119 mg, 0.778 mmol) and EDC (149 mg, 0.778 mmol) in Dichloromethane (DCM) (15 mL) stirred at 25° C. was added a solution of 1-(5-methyl-1H-pyrrolo[2,3-d]pyrimidin-4-yl)-4-piperidinamine D11a (90 mg, 0.389 mmol) and DIEA (201 mg, 1.556 mmol) in N-Methyl-2-pyrrolidone (NMP) (5 mL). The reaction mixture was stirred at 25° C. overnight. Then the mixture was washed with water (30 ml) and the organic layer was separated. The aqueous layer was extracted with DCM (20 ml×2) and the combined organic layer was concentrated.
Workup
- washThen the mixture was washed with water (30 ml)
- customthe organic layer was separated
- extractionThe aqueous layer was extracted with DCM (20 ml×2)
- concentrationthe combined organic layer was concentrated
Sources & evidence
- ORD record
- ord-02c552dd11804eb48bc13e4de0d45705
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045485B2
Reaction notes
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