Ethylamine hydrochloride → HCID 178465143, compound

HRID 550196Notes

Reaction equation

HRID 550196 reaction equation
Cl.[CH2:2]([NH2:4])[CH3:3].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[NH2:36][C:37]1[C:38]2[N:39]([C:43]([C@H:55]3[CH2:60][CH2:59][C@H:58]([C:61](O)=[O:62])[CH2:57][CH2:56]3)=[N:44][C:45]=2[C:46]2[NH:47][C:48]3[C:53]([CH:54]=2)=[CH:52][CH:51]=[CH:50][CH:49]=3)[CH:40]=[CH:41][N:42]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:36][C:37]1[C:38]2[N:39]([C:43]([C@H:55]3[CH2:60][CH2:59][C@H:58]([C:61]([NH:4][CH2:2][CH3:3])=[O:62])[CH2:57][CH2:56]3)=[N:44][C:45]=2[C:46]2[NH:47][C:48]3[C:53]([CH:54]=2)=[CH:52][CH:51]=[CH:50][CH:49]=3)[CH:40]=[CH:41][N:42]=1

Participants

7

Reactant 5

HCID 11198Ethylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178508460HCID 178508460, compound

Product 1

HCID 178465143HCID 178465143, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethylamine hydrochloride (30 mg, 0.37 mmol), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (35 mg, 0.11 mmol), and N,N-diisopropylethylamine (80 μL, 0.53 mmol) were added to a solution of trans-4-(8-Amino-1-(1H-indol-2-yl)imidazo[1,5-a]pyrazin-3-yl)cyclohexanecarboxylic acid (25 mg, 0.07 mmol) in anhydrous DMF (2 mL). Upon completion of reaction (as monitored by LCMS), the mixture was added to a saturated aqueous sodium bicarbonate solution (10 ml). The resulting precipitate was collected by filtration and washed with cold acetonitrile (3×10 mL) to afford 13 mg of the desired product. 1H NMR (d6-DMSO, 400 MHz): δ 11.41 (br s, 1H), 7.75 (dd, J=4.0, 4.0Hz, 1H), 7.69 (d, J=4.0Hz, 1H), 7.58 (d, J=8.0, 4.0Hz, 1H), 7.45 (d, J=4.0, 4.0 Hz, 1H), 7.12 (dd, J=8.0, 8.0 Hz, 1H), 7.08-7.00 (m, 2H), 6.63 (m, 1H), 6.43 (br s, 2H), 3.16 (m, 1H), 3.07 (m, 2H), 2.18 (m, 1H), 2.02 (m, 2H), 1.84 (m, 2H), 1.66 (m, 4H) and 1.02 (t, J=4.0 Hz, 3H). MS (ES+): m/z 403.09 [MH+].

Workup

  1. customUpon completion of reaction (as monitored by LCMS)
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with cold acetonitrile (3×10 mL)

Sources & evidence

ORD record
ord-f0b2fffdeab94446bcabac27f02b2322
Source dataset
uspto-grants-2011_05
Patent number
US07943767B2

Reaction notes

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