1,2-Dichloroethane → HCID 68379287, compound

HRID 403513Notes

Reaction equation

[CH2:1]([C:3]1[C:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[CH2:23][C:24]3([OH:30])[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[CH:17][CH:16]=2)=[C:6]2[N:7]=[C:8]([CH3:12])[CH:9]=[C:10]([CH3:11])[N:5]2[N:4]=1)[CH3:2].C(O[C:36]([N:38](C)[CH2:39][C:40](O)=[O:41])=O)(C)(C)C.C(Cl)C[Cl:46].C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[ClH:46].[CH2:1]([C:3]1[C:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[CH2:23][C:24]3([OH:30])[CH2:29][CH2:28][N:27]([C:40](=[O:41])[CH2:39][NH:38][CH3:36])[CH2:26][CH2:25]3)=[CH:17][CH:16]=2)=[C:6]2[N:7]=[C:8]([CH3:12])[CH:9]=[C:10]([CH3:11])[N:5]2[N:4]=1)[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

4-{(E)-3-[4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenyl]-allyl}-piperidin-4-ol (example 3) (150 mg, 0.371 mmol), 2-(tert-butoxycarbonyl (methyl)amino) acetic acid (70.2 mg, 0.371 mmol), EDC (107 mg, 0.556 mmol), HOBT (68.1 mg, 0.445 mmol) and NEt3 (0.067 ml, 0.482 mmol) were dissolved in 8 ml of DMF and stirred for 3 h at 60° C. Then the mixture was diluted with EtOAc, washed with NaCl-solution and dried over Na2 SO4. Evaporation gave a brown oil. The crude product was purified by chromatography (silicagel, EtOAc/cyclo hexane).

Workup

washwashed with NaCl-solution
customdried over Na2 SO4
customEvaporation
customgave a brown oil
customThe crude product was purified by chromatography (silicagel, EtOAc/cyclo hexane)

Sources & evidence

ORD record: ord-57d012e39c124d7eb7ade02b903f02b0
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748435B2

Reaction notes

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