1-Hydroxybenzotriazole → HCID 66781909, compound

HRID 554727Notes

Reaction equation

HRID 554727 reaction equation
NC(CC1C=CC(OC(C)(C)C)=CC=1)C(N(CC(OCC)OCC)CC1C=CC=C2C=1NN=C2)=O.[CH2:36]([NH:43][C:44](=[O:54])[NH:45][C@H:46]([CH2:51][CH:52]=[CH2:53])[CH2:47][C:48]([OH:50])=[O:49])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl.CCOC(C)=O>[CH2:36]([NH:43][C:44](=[O:54])[NH:45][CH:46]([CH2:51][CH:52]=[CH2:53])[CH2:47][C:48]([OH:50])=[O:49])[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66781561HCID 66781561, compoundHCID 66782296HCID 66782296, compound

Product 1

HCID 66781909HCID 66781909, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-Amino-3-(4-tert-butoxy-phenyl)-N-(2,2-diethoxy-ethyl)-N-(1H-indazol-7-ylmethyl)-propionamide in CH2Cl2 (50 mL) was added a solution of (3R)-3-(3-Benzyl-ureido)-hex-5-enoic acid (1.6 g, 6.1 mmol), EDCl (1.17 g, 1.2 eq), HOBt (0.93 g, 1.2 eq), DIEA (2.13 mL, 12.2 mmol) in CH2Cl2(100 mL) stirred for 40 min. The reaction mixture was stirred at room temperature for 14 h, and then diluted with EtOAc, washed with water and brine. The organic layer was dried with Na2SO4 and concentrated in vacuo. The crude compound was used next step without further purification. MS ESI 727 (M+H), 749 (M+Na)

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 14 h
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried with Na2SO4
  4. concentrationconcentrated in vacuo
  5. customwithout further purification

Sources & evidence

ORD record
ord-6a0866f9a4064a0390f14977799d7cfe
Source dataset
uspto-grants-2011_11
Patent number
US08049008B2

Reaction notes

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