Dimethylformamide → HCID 86636026, compound

HRID 449021Notes

Reaction equation

HRID 449021 reaction equation
[Cl:1][C:2]1[C:3]([CH:8]([NH2:22])[C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][N:7]=1.[CH:23]1([C:29](O)=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN(C=O)C>>[Cl:1][C:2]1[C:3]([CH:8]([NH:22][C:29]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:30])[C:9]2[CH:10]=[CH:11][C:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:13][CH:14]=2)=[N:4][CH:5]=[CH:6][N:7]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 7413Cyclohexanecarboxylic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59341168HCID 59341168, compound

Product 1

HCID 86636026HCID 86636026, compoundYield 108.3%

Procedure

In a 10 mL flask were added C-(3-chloropyrazin-2-yl)-C-(4-phenoxyphenyl)-methylamine (110 mg, 0.35 mmol), cyclohexanecarboxylic acid (0.090 g, 0.00070 mol), DIEA (0.55 mL, 0.0032 mol), TBTU (0.17 g, 0.00053 mol) and DMF (5 mL, 0.07 mol) and the reaction mixture is stirred at rt for 10 min. Reaction mixture was stirred at rt over weekend. The reaction mixture was concentrated in vacuo dissolved in DCM and washed with sat. aq NaHCO3 followed by brine. The organics were collected and concentrated in vacuo to give 160 mg of the compound as a yellow solid. Purification by prep TLC in 60% EtOAc:hexanes afforded 110 mg of the title compound as a light yellow solid. Compound was carried on to the next step. MS(ES+): m/z 422.15 (100)[MH+]. HPLC: tR=3.97 min (Open Lynx, polar—5 min).

Workup

  1. customReaction mixture
  2. stirringwas stirred at rt over weekend
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutiondissolved in DCM
  5. washwashed with sat. aq NaHCO3
  6. customThe organics were collected
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb16b44fe5c444ddaa83ef9ba102d59b
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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