Diisopropylethylamine → (S)-3-[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-1,1-bis-[3-(3-methoxycarbonylmethoxy-phenyl)-propyl]-piperidinium chloride

HRID 509908Notes

Reaction equation

HRID 509908 reaction equation
Cl.[Cl-].[NH2:3][C@H:4]1[CH2:9][CH2:8][CH2:7][N+:6]([CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])[CH:29]=2)([CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:14]=2)[CH2:5]1.[NH2:40][C:41]1[C:42]([C:49](O)=[O:50])=[N:43][C:44]([Cl:48])=[C:45]([NH2:47])[N:46]=1.C(N(CC)C(C)C)(C)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[Cl-:48].[NH2:40][C:41]1[C:42]([C:49]([NH:3][C@H:4]2[CH2:9][CH2:8][CH2:7][N+:6]([CH2:25][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])[CH:29]=3)([CH2:10][CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:14]=3)[CH2:5]2)=[O:50])=[N:43][C:44]([Cl:48])=[C:45]([NH2:47])[N:46]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 64521193,5-Diamino-6-chloro-pyrazine acidHCID 117856338(S)-3-Amino-1,1-bis-[3-(3-methoxycarbonylmethoxy-phenyl)-propyl]-piperidinium chloride hydrochloride

Product 1

HCID 117856708(S)-3-[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-1,1-bis-[3-(3-methoxycarbonylmethoxy-phenyl)-propyl]-piperidinium chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-3-Amino-1,1-bis-[3-(3-methoxycarbonylmethoxy-phenyl)-propyl]-piperidinium chloride hydrochloride (60 mg, 0.1 mmol), 3,5-Diamino-6-chloro-pyrazine-2-carboxylic acid (22 mg, 0.115 mmol) and N,N-Diisopropylethylamine (75 μl, 0.43 mmol) are dissolved in N,N-dimethylformamide (2 ml), 2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (34 mg, 0.106 mmol) is added. The reaction is stirred at room temperature overnight and purified by preparative HPLC-MS (MeOH/H2O+0.1% TFA). LC (method L): tR=1.15 min; Mass spectrum (ESI+): m/z=683 [M]+. IC50=0.025 μM

Workup

  1. custompurified by preparative HPLC-MS (MeOH/H2O+0.1% TFA)

Sources & evidence

ORD record
ord-0486180396294a588eaa0307bc3aeaef
Source dataset
uspto-grants-2015_08
Patent number
US09096548B2

Reaction notes

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