Ammonia → HCID 67216122, compound

HRID 1677574Notes

Reaction equation

HRID 1677574 reaction equation
C([N:3](CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH3:35][O:36][C:37]1[CH:38]=[C:39]([CH:54]=[CH:55][C:56]=1[N+:57]([O-:59])=[O:58])[C:40]([C:42]1[N:46]2[CH:47]=[C:48]([C:51](O)=[O:52])[CH:49]=[CH:50][C:45]2=[CH:44][N:43]=1)=[O:41].N>CN(C)C=O.O1CCCC1>[CH3:35][O:36][C:37]1[CH:38]=[C:39]([CH:54]=[CH:55][C:56]=1[N+:57]([O-:59])=[O:58])[C:40]([C:42]1[N:46]2[CH:47]=[C:48]([C:51]([NH2:3])=[O:52])[CH:49]=[CH:50][C:45]2=[CH:44][N:43]=1)=[O:41]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67215464HCID 67215464, compound

Product 1

HCID 67216122HCID 67216122, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.16 ml (1.12 mmol) of triethylamine and then 0.49 g (1.12 mmol) of BOP are added to 0.346 g (1.01 mmol) of 3-(3-methoxy-4-nitrobenzoyl)imidazo[1,5-a]pyridine-6-carboxylic acid obtained in example 182 in 10 ml of N,N-dimethylformamide. The reaction medium is stirred at ambient temperature for 30 minutes, then 1.35 ml of a 1N solution of ammonia in tetrahydrofuran are added and the mixture is stirred at ambient temperature for 18 hours. The precipitate formed is filtered off and then washed with water. 0.25 g of a yellow solid is collected. Melting point: 289° C.; 1H NMR (d6-DMSO): 4.02 (3H, s), 7.82 (1H, d), 7.98 (1H, s), 8.06-8.10 (3H, m), 8.15 (1H, s), 10.21 (1H, s)

Workup

  1. stirringthe mixture is stirred at ambient temperature for 18 hours
  2. customThe precipitate formed
  3. filtrationis filtered off
  4. washwashed with water
  5. custom0.25 g of a yellow solid is collected

Sources & evidence

ORD record
ord-3047c5cb807e4ad0b31c3d92f7c94be9
Source dataset
uspto-grants-2011_08
Patent number
US08008321B2

Reaction notes

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