Tetrahydrofuran → HCID 18381691, compound

HRID 2297485Notes

Reaction equation

HRID 2297485 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([C:19]2[S:20][CH:21]=[CH:22][N:23]=2)=[N:9][N:8]=1.C1COCC1.[NH3:30].C1COCC1>>[CH3:18][O:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[C:7]([CH2:6][CH2:5][CH2:4][C:3]([NH2:30])=[O:2])=[N:8][N:9]=[C:10]2[C:19]1[S:20][CH:21]=[CH:22][N:23]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 21982362Ammonia tetrahydrofuranHCID 543700044-(6-Methoxy-4-thiazol-2-yl-phthalazin-1-yl)-butyric acid methyl ester

Product 1

HCID 18381691HCID 18381691, compoundYield 73.1%

Conditions

Temperature
85 °C

Procedure

A suspension of 4-(6-methoxy-4-thiazol-2-yl-phthalazin-1-yl)-butyric acid methyl ester (1.2 g, 3.5 mmoles), prepared as described in example 115, in NH3/THF (10 ml) was added with THF (15 ml), then placed in autoclave at 85° C. After 1 night the mixture was dried, taken up in CH3OH (30 ml) and saturated with NH3 at 0° C., then heated at 85° C. for 44 hours. The mixture was cooled and dried to give a residue which was chromatographed (eluent: CH2Cl2/CH3OH 95:5 to 90:10). The solid was triturated in CH2Cl2 to give 840 mg of the title compound (yield: 73.1%)

Workup

  1. customprepared
  2. customplaced in autoclave at 85° C
  3. customAfter 1 night the mixture was dried
  4. customtaken up in CH3OH (30 ml) and saturated with NH3 at 0° C.
  5. temperatureThe mixture was cooled
  6. customdried
  7. customto give a residue which
  8. customwas chromatographed (eluent: CH2Cl2/CH3OH 95:5 to 90:10)
  9. customThe solid was triturated in CH2Cl2

Sources & evidence

ORD record
ord-1c4d183705aa44439aa78905d07ac0f1
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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