Triethylamine → HCID 45273206, compound

HRID 574303Notes

Reaction equation

HRID 574303 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[N:41]1([CH2:47][CH2:48][N:49]([CH2:61][CH2:62][CH3:63])[CH:50]2[CH2:59][C:58]3[CH:57]=[C:56]([OH:60])[CH:55]=[CH:54][C:53]=3[CH2:52][CH2:51]2)[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:60][C:56]1[CH:57]=[C:58]2[C:53]([CH2:52][CH2:51][CH:50]([N:49]([CH2:61][CH2:62][CH3:63])[CH2:48][CH2:47][N:41]3[CH2:42][CH2:43][N:44]([C:10]([C:6]4[CH:5]=[C:4]5[C:9](=[CH:8][CH:7]=4)[NH:1][CH:2]=[CH:3]5)=[O:12])[CH2:45][CH2:46]3)[CH2:59]2)=[CH:54][CH:55]=1

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 742801H-Indole-5-Carboxylic AcidHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 45139978HCID 45139978, compound

Product 1

HCID 45273206HCID 45273206, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Indole-5-carboxylic acid (30 mg, 0.19 mmol), EDCI (45 mg, 0.24 mmol), HOBT (31 mg, 0.24 mmol), triethylamine (31 mg, 0.32 mmol), and compound 39a (50 mg, 0.16 mmol) were dissolved in dry CH2Cl2 (10 ml) and stirred at ambient temperature overnight. The mixture was poured into sat. NaHCO3 and extracted with dichloromethane. The organic extract was dried (Na2SO4), filtered and concentrated to yield the crude product. Column chromatography afforded 40a (26 mg, 37%). 1H NMR (400 MHz, CDCl3) δ 0.87 (t, 3H, J=7.2 Hz), 1.40-1.54 (m, 3H), 1.93 (d, 1H, J=10.0 Hz), 2.45-2.78 (m, 14H), 2.86-2.91 (m, 1H), 3.70 (m, 4H), 6.45 (d, 1H, J=2.0 Hz), 6.55-6.58 (m, 2H), 6.87 (d, 1H, J=8.0 Hz), 7.21-7.24 (m, 2H), 7.33 (d, 1H, J=8.4 Hz), 7.71 (s, 1H), 8.79 (1H, bs). The free base of 40a was converted into oxalate salt. m.p. 194-199° C. Anal. [C28H38N4O.2.0(COOH)2] C, H, N.

Workup

  1. extractionextracted with dichloromethane
  2. extractionThe organic extract
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield the crude product

Sources & evidence

ORD record
ord-9fe2580011dc4db994d92cdd901d2131
Source dataset
uspto-grants-2015_05
Patent number
US09034877B2

Reaction notes

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