Tris(hydroxymethyl)aminomethane → HCID 178496434, compound

HRID 1452758Notes

Reaction equation

HRID 1452758 reaction equation
[C:1]1([C:7]2[C:14]3[S:13][C:12]([NH2:15])=[N:11][C:10]=3[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][O:17][CH2:18][C:19](Cl)=[O:20].C(O)C(N)(CO)CO>CN(C1C=CN=CC=1)C.C1COCC1>[CH3:16][O:17][CH2:18][C:19]([NH:15][C:12]1[S:13][C:14]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:8][NH:9][C:10]=2[N:11]=1)=[O:20]

Participants

6

Reactant 3

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 96623Methoxyacetyl chlorideHCID 178508260HCID 178508260, compound

Product 1

HCID 178496434HCID 178496434, compoundYield 37.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a vial charged with 3-phenyl-1H-pyrazolo[3,4-d]thiazol-5-ylamine (30 mg, 0.139 mmol), PS-DMAP (Argonaut resin, 0.56 g, 6 equiv.), and a stirring bar was added THF (2 mL) and 2-methoxyacetyl chloride (63 μL, 0.694 mmol). The reaction mixture was stirred at 70° C. for 3.5 hours, then cooled to room temperature and treated with PS-trisamine (Argonaut resin, 0.51 g, 15 equiv.) at 50° C. for 3 hours. The resin was filtered, washed with THF and the solvent was evaporated. Purification on silica gel with 0-10% MeOH in CH2Cl2 as eluent provided 15 mg (37% yield) of 2-methoxy-N-(3-phenyl-1H-pyrazolo[3,4-d]thiazol-5-yl)-acetamide as a white solid. 1H-NMR (d6-DMSO) δ: 13.6 (broad s, 1H), 12.3 (broad s, 1H), 7.73 (broad s, 2H), 7.53 (broad s, 2H), 7.37 (broad s, 1H), 4.20 (s, 2H), 3.37 (s, 3H), 2.18 (s, 3H); HPLC/MS m/z: 289.1 [MH]+.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe resin was filtered
  3. washwashed with THF
  4. customthe solvent was evaporated
  5. customPurification on silica gel with 0-10% MeOH in CH2Cl2 as eluent

Sources & evidence

ORD record
ord-09d17c39ee9243948558aed90635b803
Source dataset
uspto-grants-2009_01
Patent number
US07473783B2

Reaction notes

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