Triethylamine → HCID 57849838, compound

HRID 737214Notes

Reaction equation

HRID 737214 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.[C:9](=O)(ON1C(=O)CCC1=O)[O:10]N1C(=O)CCC1=O.C(N(CC)CC)C.[CH:34]1([NH:37][C:38]([C:40]2[CH:45]=[CH:44][C:43]([C:46]3[N:47]=[C:48]([NH:51][C:52]([C@@H:54]4[CH2:58][CH2:57][CH2:56][NH:55]4)=[O:53])[S:49][CH:50]=3)=[CH:42][CH:41]=2)=[O:39])[CH2:36][CH2:35]1>CC#N.C(Cl)Cl.CN(C1C=CN=CC=1)C>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]([N:55]2[CH2:56][CH2:57][CH2:58][CH:54]2[C:52](=[O:53])[NH:51][C:48]2[S:49][CH:50]=[C:46]([C:43]3[CH:44]=[CH:45][C:40]([C:38](=[O:39])[NH:37][CH:34]4[CH2:35][CH2:36]4)=[CH:41][CH:42]=3)[N:47]=2)=[O:10])=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 8471Triethylamine2×HCID 114724-HydroxymethylpyridineHCID 676246Di(succinimido) carbonateHCID 59228785HCID 59228785, compound

Product 1

HCID 57849838HCID 57849838, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Pyridine-4-yl-methanol (400 mg, 3.66 mmol) was dissolved in 12 mL of dry CH3CN. To this solution was added disuccinimidyl carbonate (3.66 mmol, 940 mg) followed by triethylamine (11 mmol, 1.5 mL). This solution was stirred at room temperature for 2 hours and the evaporated. The residue was redissloved in 10 mL of CH2Cl2. To this solution was added 150 mg (0.42 mmol) of pyrrolidine-2-carboxylic acid [4-(4-cyclopropyl carbamoyl-phenyl)-thiazol-2-yl]-amide (General Procedure 3I), followed by triethylamine (5.5 mmol, 0.75 mL), and DMAP (30 mg). Reaction mixture was stirred at room temperature overnight. It was evaporated to dryness, redissolved in 10 mL of DMF and purified using reverse phase HPLC. MS: 492.1(M+H+); H1 NMR (DMSO-d6): δ(ppm) 12.6 (d, 1H), 8.84 (d, 2H), 8.51 (s, 1H), 7.91 (m, 6H), 5.42 (m, 2H), 4.60 (m, 1H), 3.58 (m, 1H), 2.83 (m, 2H), 2.33 (m, 1H), 1.99 (m, 4H), 0.60 (dd, 4H).

Workup

  1. customReaction mixture
  2. stirringwas stirred at room temperature overnight
  3. customIt was evaporated to dryness
  4. dissolutionredissolved in 10 mL of DMF
  5. custompurified

Sources & evidence

ORD record
ord-b825b05364e341eb88e0ba03d9a9ba83
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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