Diisopropylethylamine → HCID 44138497, compound

HRID 1365900Notes

Reaction equation

HRID 1365900 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[F:11][C:12]1[CH:13]=[C:14]([CH:26]=[CH:27][CH:28]=1)[CH2:15][N:16]1[C:24]2[C:19](=[CH:20][C:21]([NH2:25])=[CH:22][CH:23]=2)[CH:18]=[N:17]1.C(N(C(C)C)CC)(C)C>CS(C)=O>[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([NH:25][C:21]2[CH:20]=[C:19]3[C:24](=[CH:23][CH:22]=2)[N:16]([CH2:15][C:14]2[CH:26]=[CH:27][CH:28]=[C:12]([F:11])[CH:13]=2)[N:17]=[CH:18]3)[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 842305-Pyrimidinecarboxaldehyde, 4-amino-6-chloro-HCID 71470731-(3-Fluorobenzyl)-1H-indazol-5-amine

Product 1

HCID 44138497HCID 44138497, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 4-amino-6-chloro-pyrimidine-5-carbaldehyde (95.5 mg, 0.61 mmol) and 1-(3-fluoro-benzyl)-1H-indazol-5-ylamine (147 mg, 0.61 mmol) in DMSO (1.5 mL) was added diisopropylethylamine (DIEA, 79 mg, 0.61 mmol). The mixture was stirred at 100° C. for 2 h, cooled to room temperature, then partitioned between ethyl acetate and H2O. The combined ethyl acetate extracts were dried over Na2SO4 and evaporated to afford a yellow solid, which was used in the next step without further purification.

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between ethyl acetate and H2O
  3. dry with materialThe combined ethyl acetate extracts were dried over Na2SO4
  4. customevaporated
  5. customto afford a yellow solid, which
  6. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-d4c1453e96244806b7d2699a7e34b52c
Source dataset
uspto-grants-2011_02
Patent number
US07893064B2

Reaction notes

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