Diisopropylethylamine → HCID 68946820, compound

HRID 216787Notes

Reaction equation

HRID 216787 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:8]([CH2:18][NH2:19])=[CH:7]2.Cl[C:21]1[C:22]2[CH:29]=[CH:28][NH:27][C:23]=2[N:24]=[CH:25][N:26]=1.CCN(C(C)C)C(C)C>C(O)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:8]([CH2:18][NH:19][C:21]1[C:22]3[CH:29]=[CH:28][NH:27][C:23]=3[N:24]=[CH:25][N:26]=1)=[CH:7]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 59264636HCID 59264636, compound

Product 1

HCID 68946820HCID 68946820, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Prepared according to Procedure H using (8-chloro-2-phenylquinolin-3-yl)methanamine (0.050 g, 0.186 mmol), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (0.034 g, 0.22 mmol, 1.2 eq) and DIEA (0.38 mmol, 2.0 eq) in n-butanol (3 mL). N-((8-chloro-2-phenylquinolin-3-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine [PI3Kδ IC50=270 nM] was obtained after purification as a white solid. 1H-NMR (MeOD) δ ppm 8.65-8.76 (m, 1H), 8.53 (s, 1H), 8.11-8.20 (m, 4H), 8.07 (d, J=1.96 Hz, 1H), 7.91-8.00 (m, 2H), 7.86 (s, 1H), 7.51-7.58 (m, 2H), 4.73-4.85 (m, 2H), Mass Spectrum (ESI) m/e=386 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-70a38a22a9a0413b81315166384bb56f
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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