Triethylamine → HCID 69332991, compound

HRID 1182058Notes

Reaction equation

HRID 1182058 reaction equation
[Br:1][C:2]1[C:3]([NH:18][C@H:19]([CH3:22])[CH2:20][OH:21])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[C:11]([S:14](F)(=[O:16])=[O:15])[S:12][CH:13]=2)=[N:6][CH:7]=1.[NH2:23][CH2:24][CH:25]1[CH2:27][CH2:26]1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.CC(O)CC>[CH:25]1([CH2:24][NH:23][S:14]([C:11]2[S:12][CH:13]=[C:9]([NH:8][C:5]3[N:4]=[C:3]([NH:18][CH:19]([CH3:22])[CH2:20][OH:21])[C:2]([Br:1])=[CH:7][N:6]=3)[CH:10]=2)(=[O:16])=[O:15])[CH2:27][CH2:26]1

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 75646Cyclopropanemethanamine2×HCID 58981909HCID 58981909, compound

Product 1

HCID 69332991HCID 69332991, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 6568(+-)-2-ButanolSolvent

Procedure

A reaction mixture of 130 mg (0.31 mmol) of (R)-4-[5-bromo-4-(2-hydroxy-1-methyl-ethylamino)-pyrimidin-2-ylamino]-thiophene-2-sulfonyl fluoride, 22 mg (0.31 mg) of aminomethylcyclopropane, 43 μl (0.31 mmol) of triethylamine as well as 38 mg (0.31 mmol) of DMAP in 2-butanol is stirred under reflux for 43 hours. It is mixed again with 22 mg (0.31 mg) of aminomethylcyclopropane, 43 μl (0.31 mmol) of triethylamine as well as 38 mg (0.31 mmol) of DMAP and stirred for another 24 hours under reflux. After cooling, the batch is purified by chromatography (Flashmaster II, DCM/ethanol 95:5), and the crude product that is obtained is recrystallized (ethanol/diisopropyl ether). 35 mg (0.08 mmol, 26% of theory) of the product 4-[5-bromo-4-(2-hydroxy-1-methyl-ethylamino)-pyrimidin-2-ylamino]-thiophene-2-sulfonic acid cyclopropylmethyl-amide is obtained.

Workup

  1. temperatureunder reflux for 43 hours
  2. stirringstirred for another 24 hours
  3. temperatureunder reflux
  4. temperatureAfter cooling
  5. customthe batch is purified by chromatography (Flashmaster II, DCM/ethanol 95:5)
  6. customthe crude product that is obtained
  7. customis recrystallized (ethanol/diisopropyl ether)

Sources & evidence

ORD record
ord-98c1b3b642794e8087a964cbb8c0741a
Source dataset
uspto-grants-2007_10
Patent number
US07288547B2

Reaction notes

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