Diisopropylethylamine → HCID 68157872, compound

HRID 537555Notes

Reaction equation

HRID 537555 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:22]=[C:23]([CH3:34])[C:24]=1[N:25]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[N:26]1)[O:5][CH:6]([CH:16]1[CH2:19][C:18]([CH3:21])([CH3:20])[CH2:17]1)[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1.Cl.[NH2:36][CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>O1CCCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:22]=[C:23]([CH3:34])[C:24]=1[N:25]1[CH:29]=[C:28]([C:30]([F:32])([F:31])[F:33])[CH:27]=[N:26]1)[O:5][CH:6]([CH:16]1[CH2:19][C:18]([CH3:21])([CH3:20])[CH2:17]1)[C:7]1[CH:15]=[CH:14][C:10]([C:11]([NH:36][CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[O:13])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68156518HCID 68156518, compound

Product 1

HCID 68157872HCID 68157872, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrahydrofuran (1.2 mL) was added to a vial containing 4-((3,5-dimethyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)(3,3-dimethylcyclobutyl)methyl)benzoic acid (115 mg, 0.240 mmol), ethyl 3-aminopropanoate hydrochloride (74.7 mg, 0.490 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (185 mg, 0.490 mmol). Diisopropylethylamine (0.210 mL, 1.22 mmol) was then added. The reaction was stirred for 1 h, and was then concentrated. Purification by column chromatography (0-50% ethyl acetate in heptane) afforded ethyl 3-(4-((3,5-dimethyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)(3,3-dimethylcyclobutyl)methyl)benzamido)propanoate (110 mg, 39% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.87 (s, 1H), 7.71 (d, J=8.6 Hz, 2H), 7.64 (s, 1H), 7.36 (d, J=8.2 Hz, 2H), 6.81 (t, J=4.8 Hz, 1H), 6.57 (s, 2H), 5.00 (d, J=6.8 Hz, 1H), 4.17 (q, J=7.2 Hz, 2H), 3.71 (q, J=6.1 Hz, 2H), 2.57-2.74 (m, 3H), 1.87-1.92 (m, 7H), 1.80-1.87 (m, 1H), 1.72-1.80 (m, 1H), 1.59-1.68 (m, 1H), 1.21-1.35 (m, 3H), 1.13 (s, 3H), 1.10 (s, 3H). MS (M+1): 572.3.

Workup

  1. concentrationwas then concentrated
  2. customPurification by column chromatography (0-50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-56d5625a1e7d4d38a5155597284843a3
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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