Ammonia → HCID 49764192, compound

HRID 1893247Notes

Reaction equation

HRID 1893247 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:33]=[CH:34][CH:35]=1)[C:6]([NH:8][CH2:9][C:10]([NH:12][CH:13]1[CH2:16][N:15]([CH:17]2[CH2:22][CH2:21][CH:20]([C:23]3[CH:28]=[CH:27][C:26]([CH2:29][C:30](O)=[O:31])=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)[CH2:14]1)=[O:11])=[O:7].CC[N:40]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.N>C(Cl)Cl.O1CCOCC1>[C:30]([CH2:29][C:26]1[CH:25]=[CH:24][C:23]([CH:20]2[CH2:21][CH2:22][CH:17]([N:15]3[CH2:16][CH:13]([NH:12][C:10]([CH2:9][NH:8][C:6](=[O:7])[C:5]4[CH:33]=[CH:34][CH:35]=[C:3]([C:2]([F:1])([F:36])[F:37])[CH:4]=4)=[O:11])[CH2:14]3)[CH2:18][CH2:19]2)=[CH:28][CH:27]=1)(=[O:31])[NH2:40]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 49764061HCID 49764061, compound

Product 1

HCID 49764192HCID 49764192, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of [4-(4-{3-[2-(3-trifluoromethyl-benzoylamino)-acetylamino]-azetidin-1-yl}-cyclohexyl)-phenyl]-acetic acid (as prepared in Example 25, 450 mg, 0.87 mmol), EDCI (240 mg, 1.25 mmol), HOBT (130 mg, 0.96 mmol) and TEA (610 μL, 4.35 mmol) in DCM (10 mL) was treated with 2N NH3 in dioxane (5 mL) at room temperature overnight. The solvent was removed in vacuo and the residue was purified by a CombiFlash® system using ethyl acetate and 7N NH3 in MeOH as eluent (from pure ethyl acetate to 5% 7N NH3 in MeOH in ethyl acetate) to afford the two title compound as white solids.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by a CombiFlash® system

Sources & evidence

ORD record
ord-c74ec3259d8a41f481d04169770abbf5
Source dataset
uspto-grants-2013_08
Patent number
US08513229B2

Reaction notes

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