Sodium Methoxide → HCID 178501190, compound

HRID 898036Notes

Reaction equation

HRID 898036 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@@H:29]3[CH2:34][CH2:33][C@H:32]([C:35]([O:37][CH2:38]C)=[O:36])[CH2:31][CH2:30]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]4[O:19][C:20]5[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:21]=5[N:22]=4)=[CH:13][CH:12]=3)[C:3]=12.C[O-].[Na+]>CO>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@@H:29]3[CH2:34][CH2:33][C@H:32]([C:35]([O:37][CH3:38])=[O:36])[CH2:31][CH2:30]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]4[O:19][C:20]5[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:21]=5[N:22]=4)=[CH:13][CH:12]=3)[C:3]=12

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 178472395HCID 178472395, compound

Product 1

HCID 178501190HCID 178501190, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

cis-Ethyl 4-(4-amino-3-{4-[(5,7-dimethyl-1,3-benzoxazol-2-yl)amino]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-cyclohexanecarboxylate (0.030 g, 0.057 mmol), sodium methoxide (0.0033 g, 0.063 mmol) and methanol (2 mL) were combined and heated in a resealable Schlenk tube for 48 h at 75° C. Purification of the product by preparative HPLC (25 to 100% acetonitrile in 0.1 M aqueous ammonium acetate over 20 min at 21 mL/min using an 8μ Hypersil HS C18, 250×21 mm column, Rt 15.6-16.5 min) afforded cis-methyl 4-(4-amino-3-{4-[(5,7-dimethyl-1,3-benzoxazol-2-yl)amino]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-cyclohexanecarboxylate as a white powder (0.010 g, 0.020 mmol): RP-HPLC (25 to 100% acetonitrile in 0.1 M aqueous ammonium acetate over 10 min at 1 mL/min using a 5μ Hypersil HS C18, 250×4.6 mm column) Rt 11.82 min; 1H NMR (DMSO-d6, 400 MHz) δ 10.85 (s, 1H), 8.23 (s, 1H), 7.92 (d, 2H), 7.65 (d, 2H), 7.12 (s, 1H), 6.80 (s, 1H), 4.67 (m, 1H), 3.63 (s, 3H), 3.27 (m, 1H), 2.40 (s, 3H), 2.35 (s, 3H), 2.07 (m, 6H), 1.61 (m, 2H).

Workup

  1. customPurification of the product by preparative HPLC (25 to 100% acetonitrile in 0.1 M aqueous ammonium acetate over 20 min at 21 mL/min

Sources & evidence

ORD record
ord-c79a6ba9d1904047ae49afdb45e39efa
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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