Triethylamine → HCID 58562737, compound

HRID 2175634Notes

Reaction equation

HRID 2175634 reaction equation
[C:1]([O:5][C:6](CC(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:12][CH2:13][N:14]=C=NCCCN(C)C.Cl.C1C=CC2N([OH:33])N=NC=2C=1.C(N(CC)CC)C.[NH2:41][CH:42]1[CH2:45][CH:44]([N:46]2[CH2:51][CH2:50][C:49]([C:53]3[S:57][CH:56]=[N:55][CH:54]=3)([OH:52])[CH2:48][CH2:47]2)[CH2:43]1>ClCCl>[OH:52][C:49]1([C:53]2[S:57][CH:56]=[N:55][CH:54]=2)[CH2:48][CH2:47][N:46]([CH:44]2[CH2:45][CH:42]([NH:41][C:12](=[O:33])[CH2:13][NH:14][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:43]2)[CH2:51][CH2:50]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 5458533-(Tert-butoxy)-3-oxopropanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58562832HCID 58562832, compound

Product 1

HCID 58562737HCID 58562737, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 50 mL round-bottom flask, was placed a solution of 2-(tert-butoxycarbonyl)acetic acid (899 mg, 5.14 mmol, 1.00 equiv) in dichloromethane (20 mL), EDC.HCl (1 g, 5.21 mmol, 1.10 equiv), HOBt (756 mg, 5.60 mmol, 1.10 equiv), triethylamine (1.5 g, 14.85 mmol, 3.00 equiv) and 1-(3-aminocyclobutyl)-4-(thiazol-5-yl)piperidin-4-ol (as prepared in the previous step) (1.3 g, 5.14 mmol, 1.00 equiv). The reaction mixture was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The residue purified by chromatography over a silica gel column with EtOAc/petroleum ether (1:1-1:10). The title compound was obtained as a white solid.

Workup

  1. customInto a 50 mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThe residue purified by chromatography over a silica gel column with EtOAc/petroleum ether (1:1-1:10)

Sources & evidence

ORD record
ord-971b0c91b8e145ab8c9d77c2b2476d0c
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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