Methyl Isocyanate → N-[6-Chloro-2,4,8,18,22-pentaazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-yl]-N'-methylurea bis(trifluoroacetate)

HRID 541767Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[Cl:15][C:16]1[CH:17]=[N:18][C:19]2[NH:20][C:21]3[CH:22]=[N:23][CH:24]=[C:25]([CH:38]=3)[CH2:26][CH2:27][C:28]3[CH:36]=[C:32]([NH:33][C:34]=1[N:35]=2)[CH:31]=[CH:30][C:29]=3[NH2:37].[CH3:39][N:40]=[C:41]=[O:42]>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[Cl:15][C:16]1[CH:17]=[N:18][C:19]2[NH:20][C:21]3[CH:22]=[N:23][CH:24]=[C:25]([CH:38]=3)[CH2:26][CH2:27][C:28]3[CH:36]=[C:32]([NH:33][C:34]=1[N:35]=2)[CH:31]=[CH:30][C:29]=3[NH:37][C:41]([NH:40][CH3:39])=[O:42]

Participants

Reactant 2

HCID 12228Methyl Isocyanate

HCID 866361696-Chloro-2,4,8,18,22-pentaazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-amine bis(trifluoroacetate)

Product 1

HCID 86636254N-[6-Chloro-2,4,8,18,22-pentaazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-yl]-N'-methylurea bis(trifluoroacetate)Yield 52%

Procedure

The desired compound was prepared according to the procedure of Example B83, using 6-chloro-2,4,8,18,22-pentaazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-amine bis(trifluoroacetate) and methyl isocyanate as the starting materials in 52% yield. LCMS for C19H19ClN7O (M+H)+: m/z=396.1. 1H NMR (400 MHz, DMSO-d6): δ 9.97 (s, 1H), 9.31 (s, 1H), 8.99 (m, 1H), 8.30 (m, 2H), 8.18 (s, 1H), 7.84 (m, 1H), 7.65 (d, 1H), 7.56 (d, 1H), 6.98 (dd, 1H), 6.40 (bs, 1H), 2.96 (m, 4H), 2.64 (d, 3H).

Sources & evidence

ORD record: ord-0ab670bbd9d647578e1597e32d22cffa
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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